2,2-Bis(4-chlorophenyl)ethanamine → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[2,2-bis-(4-chloro-Phenyl)-ethyl]-4-chloro-benzamide

HRID 2265179Notes

Reaction equation

HRID 2265179 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=O)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:32][NH2:33])=[CH:27][CH:26]=1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:33][CH2:32][CH:31]([C:28]3[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=3)[C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[O:18])(=[O:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 131104422,2-Bis(4-chlorophenyl)ethanamineHCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid

Product 1

HCID 115345942-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[2,2-bis-(4-chloro-Phenyl)-ethyl]-4-chloro-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid was coupled with 2,2-bis-(4-chloro-phenyl)-ethylamine as in EXAMPLE 1, Part C. HPLC: RT=11.40 min. MS (ESI−): mass calcd. for C27H19Cl3N4O3S2, 616.00; m/z found, 615/617 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.49 (s, 1H), 8.36 (dd, J=7.1, 1.0, 1H), 8.23 (dd, J=8.8, 1.0, 1H), 7.72 (dd, J=8.8, 7.0, 1H), 7.68 (d, J=1.8, 1H), 7.34-7.30 (m, 4H), 7.18-7.13 (m, 4H), 6.89 (d, J=8.4, 1H), 6.86 (dd, J=8.4, 1.8, 1H), 5.87 (br t, J=5.6, 1H), 4.24 (t, J=8.0, 1H), 3.95 (dd, J=7.9, 5.9, 2H).

Sources & evidence

ORD record
ord-9891b4b9e4554b74ad146f169d854a3d
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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