4-[(4-Methylbenzene-1-sulfonyl)amino]benzoyl chloride → (+/-)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-p-toluenesulfonamidobenzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:16][CH3:17].[C:18]1([CH3:37])[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([NH:27][S:24]([C:21]3[CH:22]=[CH:23][C:18]([CH3:37])=[CH:19][CH:20]=3)(=[O:26])=[O:25])=[CH:36][CH:35]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
6.4 g of (+/-)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene are dissolved in 150 ml of methylene chloride and 9 ml of triethylamine. A solution of 11.2 g of 4-p-toluenesulfonamidobenzoyl chloride in 200 ml of methylene chloride is added dropwise at RT in the course of 3 h, and the mixture is extracted after stirring for 1 h with 100 ml each of water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again. The organic phase is dried using sodium sulfate, concentrated and crystallized from ethyl acetate. 3.9 g (28.2% of theory) of the title compound of m.p. 174-176° C. are obtained.
Workup
- extractionthe mixture is extracted
- customThe organic phase is dried
- concentrationconcentrated
- customcrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-d413dfad26ca4e61afe3f7f6ec04f9b6
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127378
Reaction notes
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