Water → Tert-butyl 2-aminothiophene-3-carboxylate

HRID 2217157ノート

反応式

HRID 2217157 の反応式
[S:1]1CC(O)S[CH2:3][CH:2]1O.[C:9]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])#[N:10].C(N(CC)CC)C.O>O1CCCC1.C(O)(=O)C>[C:15]([O:14][C:12]([C:11]1[CH:3]=[CH:2][S:1][C:9]=1[NH2:10])=[O:13])([CH3:18])([CH3:17])[CH3:16]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 70693tert-Butyl cyanoacetateHCID 983301,4-Dithiane-2,5-diol

生成物 1

HCID 10845692Tert-butyl 2-aminothiophene-3-carboxylate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A solution of 1,4 dithiane-2,5-diol (1.1 g) and t-butyl cyanoacetate (2.2 ml) in dry tetrahydrofuran (20 ml) was warmed to ˜45° C. then treated slowly with triethylamine (2ml). The temperature rose to ˜54° C. and a yellow colouration developed. The mixture was stirred at ˜50° C. for a further 75 mins during which time the colour gradually darkened and became brownish. Water (200 ml) was added, then the mixture was acidified with acetic acid and extracted with ether. The ether extracts were washed with water, dried on magnesium sulfate, filtered and concentrated in vacuo. Residual acetic acid was removed by azeotropic distillation with toluene. The resulting brown liquid was identified as the desired product by NMR. The sample was used without further purification.

後処理

  1. customrose to ˜54° C.
  2. extractionextracted with ether
  3. washThe ether extracts were washed with water
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customResidual acetic acid was removed by azeotropic distillation with toluene
  8. customThe sample was used without further purification

出典と根拠

ORDレコード
ord-cadd76ea74b9472fb702dddd30b91233
出典データセット
uspto-grants-2008_08
特許番号
US07407954B2

反応ノート

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