Triethylamine → N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)carbodiimide

HRID 1840340Notes

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]=[C:14]([Cl:18])[C:13]=2[Cl:19])=S)=[C:4]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:3]=1[S:28]([N:31]([CH3:33])[CH3:32])(=[O:30])=[O:29].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]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[C:4]([O:20][Si:21]([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23])[C:3]=1[S:28]([N:31]([CH3:33])[CH3:32])(=[O:30])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3-dichlorophenyl)thiourea (270 mg, 0.45 mmol) in dichloromethane (10 mL) at 0° C., methanesulfonyl chloride (0.07 mL, 0.9 mmol) and triethylamine (0.13 mL, 0.9 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 (270 mg, crude). 1H NMR (CDCl3) δ 0.47 (s, 6H), 1.05 (s, 9H), 2.9 (s, 6H), 7.08 (d, 1H), 7.12 (d, 1H), 7.2 (t, 1H), 7.31 (m, 2H).

Workup

customit was partitioned between dichloromethane and water
customThe combined organic phase was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-bfaf70c54b9146e79be6736010d44fb7
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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