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

HRID 28704Notes

Reaction equation

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

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 18971875HCID 18971875, compound

Product 1

HCID 11266729N-Phenyl-N'-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)urea

Procedure

N-Phenyl-N′-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)urea was prepared from 2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride and phenyl isocyanate in a similar manner as described above to give a white solid (60% yield). 1H-NMR (DMSO-d6): δ 10.72 (s, 1H), 8.28 (s, 1H), 7.43-7.33 (m, 3H), 7.29-7.17 (m, 3H), 7.00 (m, 1H), 6.94-6.83 (m, 2H), 6.52 (d, 1H), 4.95 (m, 1H), 2.62 (m, 2H), 1.99 (m, 1H), 1.88-1.70 (m, 3H); MS m/z 304 (M−1).

Sources & evidence

ORD record: ord-701a7b786e424b27b17eeeb3c89e3815
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419997B2

Reaction notes

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