Chlorosulfonyl isocyanate → 2-Oxindole-1-carboxamide

HRID 637345ノート

反応式

HRID 637345 の反応式
ClS([N:5]=[C:6]=[O:7])(=O)=O.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17]>CCOCC>[N:8]1([C:6]([NH2:5])=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17]

参加物

4

反応物 2

HCID 70918Chlorosulfonyl isocyanateHCID 321710Oxindole

生成物 1

HCID 115172742-Oxindole-1-carboxamide収率 14.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Chlorosulfonyl isocyanate (1.20 g, 8.4 mmole) was added to a mixture of 2-oxindole (0.94 g, 7.1 mmole) in ether (30 ml) and the reaction was stirred at room temperature for 20 hours. The ether was removed under vacuum and the residue was treated with water (10 ml) and 1N HCl (10 ml). Ethyl acetate (125 ml) was added and the mixture was stirred for one hour. The ethyl acetate phase was separated, washed with 1N HCl (1×50 ml), brine (2×100 ml) and dried (MgSO4). Concentration afforded 0.97 g (77%) of crude product. Recrystallization from ethanol gave 0.18 g of the title product, m.p. 177°-179° C.

後処理

  1. customThe ether was removed under vacuum
  2. additionthe residue was treated with water (10 ml) and 1N HCl (10 ml)
  3. additionEthyl acetate (125 ml) was added
  4. stirringthe mixture was stirred for one hour
  5. customThe ethyl acetate phase was separated
  6. washwashed with 1N HCl (1×50 ml), brine (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationConcentration
  9. customafforded 0.97 g (77%) of crude product
  10. customRecrystallization from ethanol

出典と根拠

ORDレコード
ord-03ef0c9ba91a4969a63628d7bac35ad6
出典データセット
uspto-grants-1985_12
特許番号
US04556672

反応ノート

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