Benzene, 1-chloro-3-isocyanato- → HCID 52933675, compound

HRID 1024473Notes

Reaction equation

HRID 1024473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][CH:12]([CH3:35])[CH:13]([NH:18][C:19]([C:21]1[S:22][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)[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:24]3[N:25]=[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])[S:22][CH:23]=3)=[CH:27][CH:28]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933675HCID 52933675, compound

Procedure

The title compound was synthesized analogous to Example 23, using 3-chlorophenyl isocyanate and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 8.959 (s, 1H), 8.940 (s, 1H), 8.826-8.798 (d, J=8.4 Hz, 1H), 8.325 (s, 1H), 8.058-8.030 (d, J=8.4 Hz, 2H), 7.734 (s, 1H), 7.596-7.567 (d, J=8.7 Hz, 2H), 7.318-7.294 (m, 2H), 7.046-7.023 (m, 1H), 4.395-4.343 (t, J=7.8 Hz, 1H), 3.700 (s, 3H), 2.320-2.274 (m, 1H), 1.001-0.953 (t, J=6.9, 7.5 Hz, 6H); MS (ESI) m/z 485 (M−H), 487 (M+H)+.

Sources & evidence

ORD record
ord-0fa5e1a001614cd4b02bc260e4b484b4
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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