Benzene, 1-chloro-3-isocyanato- → HCID 52933176, compound

HRID 1024469Notes

Reaction equation

HRID 1024469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]=[C:9]=[O:10])[CH:3]=1.[CH3:11][CH:12]([CH3:35])[CH:13]([NH:18][C:19]([C:21]1[S:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)=[CH:24][N:25]=1)=[O:20])[C:14]([O:16][CH3:17])=[O:15]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:10])[NH:32][C:29]2[CH:30]=[CH:31][C:26]([C:23]3[S:22][C:21]([C:19]([NH:18][C@@H:13]([CH:12]([CH3:35])[CH3:11])[C:14]([O:16][CH3:17])=[O:15])=[O:20])=[N:25][CH:24]=3)=[CH:27][CH:28]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933176HCID 52933176, compound

Procedure

The title compound was synthesized analogous to Example 9, using 1-chloro-3-isocyanatobenzene and intermediate 2. 1HNMR (DMSO-d6, 300 MHz): δ 9.337 (s, 1H), 8.741-8.713 (d, 2H), 8.362 (s, 1H), 8.203-8.144 (t, J=8.7, 9 Hz, 1H), 7.744-7.716 (d, J=8.4 Hz, 2H), 7.581-7.552 (d, J=8.7 Hz, 2H), 7.507-7.463 (d, J=2.7, 11.1 Hz, 1H), 7.266-7.237 (d, J=3.7 Hz, 2H), 4.350-4.299 (t, J=7.5, 7.8 Hz, 1H), 3.681 (s, 3H), 2.306-2.238 (m, 1H), 0.965-0.923 (d, J=6.3 Hz, 6H); MS (ESI) m/z 485 (M−H), 487 (M+H)+.

Sources & evidence

ORD record
ord-52c676bea91b43d39fdf4a879e13a86f
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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