Ammonia → HCID 21537772, compound

HRID 1076603Notes

Reaction equation

HRID 1076603 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[O:4].S(Cl)([Cl:23])(=O)=O.N>ClCCl>[CH3:1][CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([Cl:23])=[CH:9][C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24648Sulfuryl chlorideHCID 21537714HCID 21537714, compound

Product 1

HCID 21537772HCID 21537772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.50 g of 2-(N-methylacetylamino)-3-(o-fluorobenzoyl)thiophene in 50 ml of dichloromethane is added dropwise 2.16 g of sulfuryl chloride in 30 ml of dichloromethane. After stirring the reaction mixture for overnight at room temperature, the reaction mixture is neutralized with aqueous ammonia, then extracted with methylene chloride. The methylene chloride extracts are washed with water, dried over sodium sulfate, then evaporated under reduced pressure to a residue. The residue is chromatographed on silica gel using chloroform as an eluent to give 2-(N-methylacetylamino)-3-(o-fluorobenzoyl)-5-chlorothiophene as an oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride extracts are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure to a residue
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-0ded6b71978148f8bf02a2e265a73301
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

Loading…