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

HRID 1840339ノート

反応式

HRID 1840339 の反応式
[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]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23447779N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2-bromophenyl)thiourea

生成物 1

HCID 23447747N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaninosulfonyl)phenyl]-N'-(2-bromophenyl)carbodiimide収率 116.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  1. customit was partitioned between dichloromethane and water
  2. customThe combined organic phase was dried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-06ccfa75970247769c43bfdc96de83cc
出典データセット
uspto-grants-2004_01
特許番号
US06680317B2

反応ノート

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