N-(5-Chloro-2-methoxyphenyl)thiourea → 2-(5-Chloro-2-methoxyphenylamino)-4,5,6,7-tetrahydrocyclohepta[d]thiazol-8-one

HRID 1942998Notes

Reaction equation

HRID 1942998 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:24][CH3:25])=[C:18](NC(N)=S)[CH:19]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:24][CH3:25])=[C:16]([NH:1][C:2]2[S:3][C:4]3[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=3[N:6]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 2732660N-(5-Chloro-2-methoxyphenyl)thioureaHCID 251308282-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one

Product 1

HCID 251311462-(5-Chloro-2-methoxyphenylamino)-4,5,6,7-tetrahydrocyclohepta[d]thiazol-8-oneYield 26%

Procedure

Following the procedure described for 26z by condensing 5-chloro-2-methoxyphenylthiourea gave 30z (light brown solid; 26% for two steps). 1H NMR (600 MHz, DMSO-d6): δ 7.81 (d, J=2.4 Hz, 1H), 7.75 (dd, J=9 Hz, 2.4 Hz, 1H), 7.42 (d, J=9 Hz, 1H), 3.83 (s, 3H), 2.84-2.75 (m, 2H), 2.58-2.52 (m, 1H), 2.33-2.28 (m, 1H), 1.90-1.74 (m, 4H). 13C NMR (150 MHz, DMSO-d6): δ 194.4, 169.8, 154.5, 148.9, 134.1, 130.2, 125.7, 122.6, 121.7, 116.3, 57.6, 42.9, 30.5, 24.4, 21.5.

Sources & evidence

ORD record
ord-54cfb37981694aa482e7a94cf71dac0c
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

Loading…