Reactions of chromone-3-carbaldehydes (1) with 2-aminobenzothiazoles (2) in alcohols (20 mL) at 30–40 °C.

Entry	1	2	Alcohol	Time (h)	Product	Yield (%)
1	H	H	MeOH	10	3aa	90
2	H	6-Br	MeOH	10	3ab	88
3	H	6-OMe	MeOH	10	3ac	91
4	H	4,6-F2	MeOH	10	3ad	79
5	6-Cl	H	MeOH	10	3ae	86
6	6-Br	H	MeOH	10	3af	83
7	6-Cl	6-OMe	MeOH	10	3ag	89
8	6-Cl	6-OCF3	MeOH	10	3ah	82
9	6-Cl	4,6-F2	MeOH	10	3ai	83
10	6-Cl	6-Br	MeOH	10	3aj	88
11	6-Cl	6-Me	MeOH	10	3ak	91
12	6-Br	6-Br	MeOH	10	3al	92
13	6-Br	4,6-F2	MeOH	10	3am	87
14	6-Br	5-Cl-7-F	MeOH	10	3an	88
15	6-OH	H	MeOH	10	3ao	82
16	6-Cl-8-Br	4-Cl	MeOH	10	3ap	84
17	H	H	EtOH	12	3aq	85
18	H	6-OMe	EtOH	12	3ar	83
19	H	4-Cl	EtOH	12	3as	84
20	6-Br	6-Me	EtOH	12	3at	86
21	6-Cl	4-Cl	1-Propanol	24	3au	79
22	6-Cl	4-Cl	1-Butanol	48	3av	75
23	6-Cl	6-OMe	1-Butanol	48	3aw	76
24	6-Cl	4-Cl	1-Hexanol	96	3ax	64
25	6-Cl	4-Cl	1-Heptanol	96	3ay	59
26	6-Cl	4-Cl	1-Octanol	144	3az	38
27	H	4-Cl	Isobutanol	48	3ba	74
28	6-Cl	4-Cl	Isobutanol	48	3bb	78
29	6-Cl	H	1,2-Ethanediol	24	3bc	76
30	6-Cl	4-Cl	1,5-Pentanediol	72	3bd	53
31	6-NO2	H	MeOH	24	—a	—
32	H	6-NO2	MeOH	24	—b	—
33	H	H	2-Propanol	6	4a	95
34	H	6-Me	2-Propanol	6	4b	95
35	6-Cl	H	2-Propanol	6c	4c	96
36	6-Br	H	2-Propanol	6c	4d	95
37	6-OH	H	2-Propanol	6	4e	96
38	6-Cl	4-Cl	2-Butanol	48	3be	74
39	H	4-Cl	2-Butanol	48	3bf	76
40	6-Cl	4-Cl	Cyclohexanol	48	3bg	45
41	6-Cl	—d	MeOH	24	3bh	29

^aDifficult to purify.

^bNo reaction.

^cReaction completed in 2 h under reflux.

^d4-Chloroaniline.