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

HRID 2217157

반응식

HRID 2217157 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cadd76ea74b9472fb702dddd30b91233
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407954B2

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