Triethylamine → N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaninosulfonyl)phenyl]-N'-(2-bromophenyl)carbodiimide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=S)=[C:4]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:3]=1[S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28].CS(Cl)(=O)=O.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[C:4]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[C:3]=1[S:27]([N:30]([CH3:32])[CH3:31])(=[O:28])=[O:29]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-bromophenyl)thiourea (240 mg, 0.42 mmol) in dichloromethane (10 mL) at 0° C., methanesulfonyl chloride (0.065 mL, 0.84 mmol) and triethylamine (0.12 mL, 0.84 mmol) were added. 4-Dimethylaminopyridine was added as a catalyst. The reaction mixture was stirred at 0° C. for 1 hour, then it was partitioned between dichloromethane and water. The combined organic phase was dried and concentrated to give the desired product (266.2 mg, crude). 1H NMR (CDCl3) δ 0.4 (s, 6H), 1.09 (s, 9H), 2.86 (s, 6H), 7.06 (d, 2H), 7.1-7.37 (m, 4H).
Workup
- customit was partitioned between dichloromethane and water
- customThe combined organic phase was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-06ccfa75970247769c43bfdc96de83cc
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680317B2
Reaction notes
Loading…