4(5H)-Thiazolone, 2-amino- → 4-[4-(2-Amino-4-oxo-4H-thiazol-5-ylidenemethyl)-2-methoxy-phenoxy]-3-chloro-benzonitrile

HRID 2040097Notes

Reaction equation

HRID 2040097 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C:5](=[O:7])[N:6]=1.[Cl:8][C:9]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:10]=1[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[O:20][CH3:21]>>[NH2:1][C:2]1[S:3][C:4](=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][C:10]3[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:9]=3[Cl:8])=[C:13]([O:20][CH3:21])[CH:14]=2)[C:5](=[O:7])[N:6]=1

Participants

3

Reactant 2

HCID 111754(5H)-Thiazolone, 2-amino-HCID 510515014-(2-Chloro-4-cyanophenoxy)-3-methoxybenzaldehyde

Product 1

HCID 692728854-[4-(2-Amino-4-oxo-4H-thiazol-5-ylidenemethyl)-2-methoxy-phenoxy]-3-chloro-benzonitrile

Procedure

4-[4-(2-Amino-4-oxo-4H-thiazol-5-ylidenemethyl)-2-methoxy-phenoxy]-3-chloro-benzonitrile was prepared using 2-amino-thiazol-4-one and 4-(2-Chloro-4-cyanophenoxy)-3-methoxybenzaldehyde according to General Procedure B. 1H NMR (400 Hz, DMSO-d6) δ 9.47 (bs, NH), 9.21 (bs, NH), 8.17 (d, 1H), 7.70 (dd, 1H), 7.64 (s, 1H), 7.46 (d, 1H), 7.32 (d, 1H), 7.23 (dd, 1H), 6.81 (d, 1H), 3.79 (s, 3H); LC/MS (m/z) [M+1]+386.0 (calculated for C18H13ClN3O3S, 386.82).

Sources & evidence

ORD record
ord-af827a14cd8f4d3a8cdc9c36fc33bfd7
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

Loading…