P,P-Diphenylphosphinodithioic acid → 3-Amino-3-[4-(1,1-difluoroethyl)-phenyl]thioacrylamide

HRID 2422709Notes

Reaction equation

HRID 2422709 reaction equation
C1(P(C2C=CC=CC=2)(S)=[S:8])C=CC=CC=1.[NH2:16][C:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[CH3:28])=[CH:23][CH:22]=1)=[CH:18][C:19]#[N:20]>CC(O)C.CCOC(C)=O>[NH2:16][C:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[CH3:28])=[CH:23][CH:22]=1)=[CH:18][C:19]([NH2:20])=[S:8]

Participants

5

Reactant 2

HCID 129564P,P-Diphenylphosphinodithioic acidHCID 67179938HCID 67179938, compound

Product 1

HCID 866326533-Amino-3-[4-(1,1-difluoroethyl)-phenyl]thioacrylamideYield 67.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Add diphenylphosphinodithioic acid (13.2 g, 52.9 mmol) to a solution of 3-amino-3-[4-(1,1-difluoroethyl)phenyl]acrylonitrile (5.50 g, 26.4 mmol) in propan-2-ol (264 mL). Heat to 45° C. for 4 h. Dilute with EtOAc (400 mL), wash with brine 3× (100 mL), and evaporate. Crystallize from EtOAc/hexane to afford 3-amino-3-[4-(1,1-difluoroethyl)-phenyl]thioacrylamide. Yield: 67.2%. ES-MS: m/e 243.0 (m+1).

Workup

  1. washwash with brine 3× (100 mL)
  2. customevaporate
  3. customCrystallize from EtOAc/hexane

Sources & evidence

ORD record
ord-18afdd9e68fe46b7982c1a289e3bf835
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

Loading…