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

HRID 2422700Notes

Reaction equation

HRID 2422700 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-e8d0372d76de4bfc8953f5314ca0c91d
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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