Thionyl Chloride → HCID 507310, compound

HRID 1938849Notes

Reaction equation

HRID 1938849 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[O:7][CH2:8][CH2:9][S:10][C:11]=1[C:12]([OH:14])=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(Cl)Cl>[CH3:5][C:6]1[O:7][CH2:8][CH2:9][S:10][C:11]=1[C:12]([NH:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acidHCID 12607966Ethyl 3-amino-4-methylbenzoate

Product 1

HCID 507310HCID 507310, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (4.5 g, 0.038 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (6.0 g, 0,037 mole) and methylene chloride (100 ml). The mixture was warmed to 30°-35° C. for 3 hours, then evaporated under reduced pressure. The residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml), and the ice-chilled solution treated dropwise with a solution of ethyl 3-amino-4-methylbenzoate (6.7 g, 0,037 mole) and tziethylamine (4.0 g, 0,040 mole) in methylene chloride (100 ml). The reaction mixture was stirred overnight at room temperature and then worked up by washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water. Evaporation of the solvent gave an oil, which solidified. After recrystallization from ethanol (30 ml), the product (7.1 g, 59% yield) melted at 105°-107° C.

Workup

  1. temperatureThe mixture was warmed to 30°-35° C. for 3 hours
  2. customevaporated under reduced pressure
  3. dissolutionThe residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml)
  4. temperaturethe ice-chilled solution
  5. washby washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water
  6. customEvaporation of the solvent
  7. customgave an oil, which
  8. customAfter recrystallization from ethanol (30 ml)

Sources & evidence

ORD record
ord-175bbec288ce4b0ca20a1582a8ae151c
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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