Hydrochloric Acid → 3-Amino-3-(4-methoxyphenyl)-2-methyl-thioacrylamide

HRID 2422700노트

반응식

HRID 2422700 반응식
Cl.[NH2:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[C:4]([CH3:7])[C:5]#[N:6].C(N)(=[S:18])C>O1CCOCC1>[NH2:2][C:3]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[C:4]([CH3:7])[C:5]([NH2:6])=[S:18]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2723949ThioacetamideHCID 534010953-Amino-3-(4-methoxyphenyl)-2-methylprop-2-enenitrile

생성물 1

HCID 730126063-Amino-3-(4-methoxyphenyl)-2-methyl-thioacrylamide수율 90.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Add HCl (4 N in dioxane, 659 mL, 2.640 mmol) to a solution of 3-amino-3-(4-methoxyphenyl)-2-methylacrylonitrile (24.8 g, 132 mmol), thioacetamide (19.8 g, 264 mmol) and dioxane (132 mL) under dry nitrogen. Stir for 2 h. Evaporate, dilute the solid with dioxane (20 mL) and add dry TEA (40 mL). Add satd K2CO3 and extract with EtOAc. Evaporate the organic solution and crystallize from CHCl3/hexane (95/5); then recrystallize from MeOH/H2O to remove the excess thioacetamide to afford 3-amino-3-(4-methoxyphenyl)-2-methyl-thioacrylamide. Yield: 90.8%.

후처리

  1. customEvaporate
  2. additiondilute the solid with dioxane (20 mL)
  3. additionadd dry TEA (40 mL)
  4. additionAdd satd K2CO3
  5. extractionextract with EtOAc
  6. customEvaporate the organic solution
  7. customcrystallize from CHCl3/hexane (95/5)
  8. customthen recrystallize from MeOH/H2O
  9. customto remove the excess thioacetamide

출처 및 근거

ORD 기록
ord-e8d0372d76de4bfc8953f5314ca0c91d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960419B2

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