Hydrochloric Acid → HCID 10469837, compound

HRID 2108087Notes

Reaction equation

HRID 2108087 reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.C[O-].[Na+].[CH3:10][O:11][C:12]1[C:13]([O:24][CH3:25])=[CH:14][C:15]2[S:21][CH2:20][CH2:19][CH2:18][C:17](=[O:22])[C:16]=2[CH:23]=1.Cl>>[CH3:10][O:11][C:12]1[C:13]([O:24][CH3:25])=[CH:14][C:15]2[S:21][CH2:20][CH2:19][CH:18]([C:1]([O:4][CH3:5])=[O:6])[C:17](=[O:22])[C:16]=2[CH:23]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 9991793HCID 9991793, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10469837HCID 10469837, compoundYield 79%

Procedure

To dimethyl carbonate (87 g) is added sodium methoxide (10.5 g), to the mixture is added 7,8-dimethoxy-3,4-dihydro-1-benzothiepin-5(2H)-one(11.0 g) obtained in Reference Example 7. The mixture is heated for two hours under reflux. The reaction mixture is poured into ice-water and acidified (pH 3) with 2N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer is washed with a saturated aqueous saline solution, dried, and concentrated under reduced pressure. The residue is recrystallized from hexane - methylene chloride to afford methyl 7,8-dimethoxy5-oxo-2,3,4,5-tetrahydro-1-benzothiepin-4-carboxylate as colorless needles (10.8 g), m.p. 132°-133° C.

Workup

  1. customobtained in Reference Example 7
  2. temperatureThe mixture is heated for two hours
  3. temperatureunder reflux
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer is washed with a saturated aqueous saline solution
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is recrystallized from hexane - methylene chloride

Sources & evidence

ORD record
ord-5b7b7d9af5e048bf81c460fe471c97ec
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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