Triethylamine → 6-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one

HRID 2308936Notes

Reaction equation

HRID 2308936 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:12]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[CH:15][N:16]([CH3:18])[CH3:17])[C:7](=[O:11])[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 2480656-Chlorothiochroman-4-one

Product 1

HCID 38135366-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6-chloro-2,3-dihydro-4H-1-benzothiopyran-4-one (30 g), N,N-dimethylformamide dimethyl acetal (80 ml), and triethylamine (31.4 ml) in benzene (400 ml) was refluxed with stirring for 1 hour and then about three-fourths of the solvent were distilled slowly at atmospheric pressure over a period of approximately 1 hour. Benzene (300 ml) was added to the reaction mixture and the solvent was distilled again. To the residue was added diethyl ether (150 ml) and the mixture was triturated to give 6-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one (34 g).

Workup

  1. distillationabout three-fourths of the solvent were distilled slowly at atmospheric pressure over a period of approximately 1 hour
  2. additionBenzene (300 ml) was added to the reaction mixture
  3. distillationthe solvent was distilled again
  4. additionTo the residue was added diethyl ether (150 ml)
  5. customthe mixture was triturated

Sources & evidence

ORD record
ord-e9d86e1fce0949b381afb289ab19606f
Source dataset
uspto-grants-1987_09
Patent number
US04692444

Reaction notes

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