2,6-Dichlorobenzoyl chloride → N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2,6-dichlorobenzamide

HRID 28685

Reaction equation

HRID 28685 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:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:18]=1[C:19](Cl)=[O:20]>>[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:19](=[O:20])[C:18]3[C:17]([Cl:16])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:26])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11774976N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2,6-dichlorobenzamide

Procedure

N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2,6-dichlorobenzamide was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine and 2,6-dichlorobenzoyl chloride in a similar manner as described above to give a white solid (25% yield). 1H-NMR (DMSO-d6): δ 10.80 (s, 1H), 9.18 (d, 1H), 7.61 (d, 1H), 7.52 (d, 1H), 7.49 (d, 1H), 7.43 (dd, 1H), 7.36 (d, 1H), 7.19 (dd, 1H), 5.27 (m, 1H), 2.69 (m, 2H), 2.08-1.82 (m, 4H); MS m/z 437 (M−1).

Sources & evidence

ORD record
ord-24450dfee6a149a98d981a20517f275c
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Linked notes

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