4(5H)-Thiazolone, 2-amino- → CID 140529017

HRID 2040098Notes

Reaction equation

HRID 2040098 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C:5](=[O:7])[N:6]=1.[Cl:8][C:9]1[CH:27]=[C:26]([CH:28]=C2SC(=O)NC2=O)[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[C:20]([F:23])([F:22])[F:21]>>[Cl:8][C:9]1[CH:27]=[C:26]([CH:28]=[C:4]2[S:3][C:2](=[NH:1])[NH:6][C:5]2=[O:7])[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[C:20]([F:21])([F:22])[F:23]

Participants

3

Reactant 2

HCID 111754(5H)-Thiazolone, 2-amino-HCID 743876324-[2-Chloro-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenoxy]-3-trifluoromethylbenzonitrile

Product 1

HCID 140529017CID 140529017

Procedure

4-[2-Chloro-4-(2-imino-4-oxo-thiazolidin-5-ylidenemethyl)-phenoxy]-3-trifluoromethyl-benzonitrile was prepared using 2-amino-thiazol-4-one and 4-[2-Chloro-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenoxy]-3-trifluoromethylbenzonitrile according to General Procedure C. 1H NMR (400 MHz, DMSO-d6) δ 9.56 (br, 1H), 9.24 (br, 1H), 8.40 (d, J=1.56 Hz, 1H), 8.08 (dd, J=8.6 and 1.95 Hz, 1H), 7.90 (d, J=1.96 Hz, 1H), 7.65 (d, J=2.35 Hz, 1H), 7.63 (s, 1H), 7.50 (d, J=8.61 Hz, 1H), 7.07 (d, J=8.61 Hz, 1H). LC/MS (m/z) [M+1]+424.2 (calculated for C18H10ClF3N3O2S 424.0).

Sources & evidence

ORD record
ord-8720163e05d04eb4972b6a472dd998f2
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

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