Hydrochloric Acid → HCID 19087513, compound

HRID 1613098Notes

Reaction equation

HRID 1613098 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH3:17])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=[O:15].Cl[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>C(#N)C.O>[C:7]1([CH3:17])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 69519o-Tolylacetic acid

Product 1

HCID 19087513HCID 19087513, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (25 g) was added to a stirred solution of o-tolylacetic acid (7.5 g) in acetonitrile (125 ml). The mixture was stirred for ten minutes at room temperature. Ethyl chloroacetate (6.13 g) was added and the mixture heated at reflux overnight. It was then poured into water, acidified with concentrated hydrochloric acid to pH2 and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated, and purified by column chromatography to give ethoxycarbonylmethyl o-tolylacetate. Potassium carbonate (15 g) was added to a stirred solution of this product (10 g) in dimethylformamide (100 ml). The mixture was stirred at room temperature for 72 hours and then heated at reflux overnight. The mixture was cooled to 0° C. and potassium carbonate (5 g) added, followed by methyl iodide (2.65 ml). The mixture was stirred at room temperature for 24 hours. The mixture was poured into water, extracted with ether and the extract washed with brine, dried and evaporated to give 3-(2-methylphenyl)-4-methoxyfuran-2(5 H)-one, as a gum. This was then treated with N-bromosuccinimide followed by reaction with 2-mercaptobenzothiazole, in a similar manner to that described in Example 1, to give 3-[2-[[(2-benzothiazolyl)-thio]methyl]phenyl]-4-methoxyfuran-2(5H)-one, m.p. 81°-82°. (Compound 2).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-0cdfff60c70a45ceb195753a24d43c72
Source dataset
uspto-grants-1993_03
Patent number
US05192357

Reaction notes

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