Dicyclohexylcarbodiimide → N-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide

HRID 344582

反応式

HRID 344582 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34]([C:40](O)=[O:41])[N:33]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34]([C:40]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:13])=[O:12])=[O:41])[N:33]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 42546Benzoic acid, 2-(aminosulfonyl)-, methyl esterHCID 44224834,6-Dimethoxypyrimidine-2-carboxylic acid

生成物 1

HCID 14580647N-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide

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

2.2 g of 2-methoxycarbonylbenzenesulfonamide are added in portions at 0° C. to 2° C. to a mixture of 2.3 g of dicyclohexylcarbodiimide, 120 mg of 4-dimethylaminopyridine and 2.2 g of 4,6-dimethoxypyrimidine-2-carboxylic acid in 80 ml of absolute dichloromethane. The mixture is stirred for 0.5 hour at 0° C. and 2 hours at room temperature, and allowed to stand overnight. The urea which has precipitated is filtered off, the filtrate is concentrated in vacuo, and the residue is stirred for 0.5 hour with 100 ml of 2 N sodium carbonate solution. The aqueous phase is extracted using ether, and a pH of 2-3 is established using concentrated hydrochloric acid. The product which has precipitated is filtered off with suction and dried in vacuo. This gives 1.3 g of N-(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide of melting point 163°-165° C. (from ethyl acetate).

後処理

  1. waitto stand overnight
  2. customThe urea which has precipitated
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. stirringthe residue is stirred for 0.5 hour with 100 ml of 2 N sodium carbonate solution
  6. extractionThe aqueous phase is extracted
  7. customThe product which has precipitated
  8. filtrationis filtered off with suction
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-0015cf6429ba4281ae343ec9520b699d
出典データセット
uspto-grants-1991_10
特許番号
US05053072

関連ノート

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