2-Chloro-4-isocyanatoanisole → N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-N'-(3-chloro-4-methoxyphenyl)urea

HRID 28678

Reaction equation

HRID 28678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[Cl:16][C:17]1[CH:18]=[C:19]([N:25]=[C:26]=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:26]([NH:25][C:19]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([Cl:16])[CH:18]=3)=[O:27])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 1199472-Chloro-4-isocyanatoanisoleHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11419514N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-N'-(3-chloro-4-methoxyphenyl)urea

Procedure

N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-N′-(3-chloro-4-methoxyphenyl)urea was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine and 3-chloro-4-methoxyphenyl isocyanate in a similar manner as described above to give a tan solid (42% yield). 1H-NMR (DMSO-d6): δ 10.98 (s, 1H), 8.33 (s, 1H), 7.73 (d, 1H), 7.60 (d, 1H), 7.30 (d, 1H), 7.25-7.14 (m, 2H), 7.08 (d, 1H), 6.63 (d, 1H), 5.01 (m, 1H), 3.82 (s, 3H), 2.65 (m, 2H), 2.04 (m, 1H), 1.94-1.76 (m, 3H); MS m/z 448 (M−1).

Sources & evidence

ORD record
ord-a9ba3fc031054932bfbd7a8f6da9c0f1
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Linked notes

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