Ammonium Acetate → HCID 178517451, compound

HRID 1414510Notes

Reaction equation

HRID 1414510 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[O:4].C([O-])(=O)C.[NH4+:26]>CS(C)=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[NH:5][C:3](=[O:4])[N:26]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 21487723HCID 21487723, compound

Product 1

HCID 178517451HCID 178517451, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 2.11 g of 2-trichloroacetamido-3-(o-fluorobenzoyl)thiophene in 18 ml of dimethylsulfoxide was added 0.89 g of ammonium acetate. The mixture was heated at 95° C for 2 hours and poured into ice water, and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on 60 g of Silica gel, using ethyl acetate as an eluent to obtain 4-(o-fluorophenyl)-1,2-dihydrothieno(2,3-d)-pyrimidin-2-one as crystals having a melting point of 272°-275° C. Recrystallization from acetone gave crystals melting at 247.5°- 249° C. The following compounds were prepared similarly:

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed on 60 g of Silica gel

Sources & evidence

ORD record
ord-8bae8b5c4fe74aa6bdcd2f729d5f7d62
Source dataset
uspto-grants-1977_01
Patent number
US04001412

Reaction notes

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