Hydrochloric Acid → 3-Amino-3-(3-fluoro-4-methoxyphenyl)thioacrylamide

HRID 2422708Notes

Reaction equation

HRID 2422708 reaction equation
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([F:14])[CH:7]=1)=[CH:3][C:4]#[N:5].C(N)(=[S:17])C.Cl>O1CCOCC1>[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([F:14])[CH:7]=1)=[CH:3][C:4]([NH2:5])=[S:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723949ThioacetamideHCID 671792423-Amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrile

Product 1

HCID 866326523-Amino-3-(3-fluoro-4-methoxyphenyl)thioacrylamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add dioxane (65 mL) to 3-amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrile (25.0 g, 130 mmol) and thioacetamide (19.5 g, 260 mmol); then add 4 N HCl in dioxane (650 mL, 2,600 mmol) and allow the reaction to stir 4-8 h until complete by TLC. Evaporate the reaction mixture to dryness; then add dioxane (200 mL); add slowly TEA (dried with K2CO3, 1000 mL); and then add satd K2CO3 (1000 mL) and extract with EtOAc (2000 mL). Dry the organic phase (K2CO3) and evaporate to afford 3-amino-3-(3-fluoro-4-methoxyphenyl)thioacrylamide. Yield: 98.5%. ES-MS: m/e 227.0 (m+1).

Workup

  1. customthe reaction
  2. customEvaporate the reaction mixture to dryness
  3. additionadd slowly TEA (dried with K2CO3, 1000 mL)
  4. additionand then add satd K2CO3 (1000 mL)
  5. extractionextract with EtOAc (2000 mL)
  6. dry with materialDry the organic phase (K2CO3)
  7. customevaporate

Sources & evidence

ORD record
ord-c464f991343146c88738ecc251339d1e
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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