Dimethylformamide dimethyl acetal → HCID 69449912, compound

HRID 1370171Notes

Reaction equation

HRID 1370171 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[C:8]2[C:3]=1[C:4](=[O:16])[CH2:5][CH2:6][S:7]2.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[C:8]2[C:3]=1[C:4](=[O:16])[C:5](=[CH:19][N:20]([CH3:22])[CH3:21])[CH2:6][S:7]2

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 21933604HCID 21933604, compound

Product 1

HCID 69449912HCID 69449912, compoundYield 97%

Procedure

30 g (0.078 mol) of methyl 5-chloro-4-oxothiochromane-8-carboxylate in 300 ml of N,N-dimethylformamide dimethyl acetal were heated under reflux for 6 hours. Volatile components were then distilled off, the residue was taken up in methylene chloride and the organic phase was washed with water. Drying and removal of the solvent gave 35.3 g (97%) of methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate.

Workup

  1. temperatureunder reflux for 6 hours
  2. distillationVolatile components were then distilled off
  3. washthe organic phase was washed with water
  4. customDrying
  5. customremoval of the solvent

Sources & evidence

ORD record
ord-95c33af2caae49e08a7662d207d7e078
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

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