Triethylamine → 3-(N-tert-Butoxylcarbonyl-N-methylamino)phenyl isocyanate

HRID 2341

反応式

HRID 2341 の反応式
CC[N:3]([CH2:6]C)CC.ClC(OCC)=[O:10].[O:14]([C:19]([N:21]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)C(O)=O)[CH3:22])=[O:20])[C:15]([CH3:18])([CH3:17])[CH3:16].[N-]=[N+]=[N-].[Na+]>CC(C)=O.O.C1(C)C=CC=CC=1>[O:14]([C:19]([N:21]([C:23]1[CH:24]=[C:25]([N:3]=[C:6]=[O:10])[CH:29]=[CH:30][CH:31]=1)[CH3:22])=[O:20])[C:15]([CH3:16])([CH3:17])[CH3:18]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 223491653-(N-Boc-N-methylamino)benzoic acid

生成物 1

HCID 212018273-(N-tert-Butoxylcarbonyl-N-methylamino)phenyl isocyanate収率 78.5%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

Et3N (3.71 g, 36.7 mmol) and a solution of ethyl chloroformate (4.31 g, 39.7 mmol) in acetone (10 ml) were successively added dropwise to a solution of 3-(N-tert-butoxylcarbonyl-N-methylamino)benzoic acid (8.0 g, 31.8 mmol) in acetone (64 ml) below 5° C. After stirring for 30 min, a solution of NaN3 (3.10 g, 47.7 mmol) in water (10 ml) was added to the solution below 5° C. The mixture was stirred at the same temperature for a further 1 h, then poured into toluene (80 ml) and water (160 ml). The organic portion was washed with brine, refluxed for 2 h and evaporated. The residue was distilled (100°-105° C./0.9-1.0 mmHg) to afford the title compound (6.2 g, 78%) as a yellow oil.

後処理

  1. stirringThe mixture was stirred at the same temperature for a further 1 h
  2. washThe organic portion was washed with brine
  3. temperaturerefluxed for 2 h
  4. customevaporated
  5. distillationThe residue was distilled (100°-105° C./0.9-1.0 mmHg)

出典と根拠

ORDレコード
ord-b0e3813329fd4701a3a3f986ee306d00
出典データセット
uspto-grants-1998_03
特許番号
US05728829

関連ノート

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