Phenyl isocyanate → N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)N'-phenylurea

HRID 28706Notes

Reaction equation

HRID 28706 reaction equation
[Cl: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.[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Cl: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:23]([NH:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:24])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 177434976-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11450646N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)N'-phenylurea

Procedure

N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-N′-phenylurea was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine and phenyl isocyanate in a similar manner as described above to give a white solid (74% yield). 1H-NMR (DMSO-d6): δ 10.93 (s, 1H), 8.30 (s, 1H), 7.41-7.36 (m, 3H), 7.28 (d, 1H), 7.21 (m, 2H), 7.00 (dd, 1H), 6.88 (m, 1H), 6.57 (d, 1H), 4.95 (m, 1H), 2.59 (m, 2H), 1.98 (m, 1H), 1.88-1.70 (m, 3H); MS m/z 338 (M−1).

Sources & evidence

ORD record
ord-431ad0862276437ea4e716328d035ea6
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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