Triethylamine → HCID 507307, compound

HRID 1938843Notes

Reaction equation

HRID 1938843 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][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C>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][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 24386Thionyl ChlorideHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

Product 1

HCID 507307HCID 507307, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (6.5 g, 0.055 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (8.0 g, 0.050 mole) and methylene chloride (50 ml). The mixture was warmed to 35°-40° C. for 4 hours and the resulting dark solution evaporated under reduced pressure. The solid residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (50 ml). On the following day, the solution was treated dropwise at 15°-20° C. over 2 hours with a solution of ethyl 3-aminobenzoate (8.2 g, 0.050 mole) and triethylamine (5.5 g, 0.054 mole) in methylene chloride (50 ml). The reaction mixture was stirred at room temperature for a further 5 hours and worked up by washing in sequence with water (50 ml), dilute hydrochloric acid (3.5%, 50 ml), water (50 ml), dilute sodium hydroxide (2%, 25 ml) and water (50 ml). Evaporation of the solvent left an oil, which slowly solidified. Recrystallization from ethanol (75 ml) gave yellow-tan crystals, m.p. 100°-102° C. (11.2 g, 73% yield).

Workup

  1. temperatureThe mixture was warmed to 35°-40° C. for 4 hours
  2. customthe resulting dark solution evaporated under reduced pressure
  3. dissolutionThe solid residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (50 ml)
  4. washby washing in sequence with water (50 ml), dilute hydrochloric acid (3.5%, 50 ml), water (50 ml), dilute sodium hydroxide (2%, 25 ml) and water (50 ml)
  5. customEvaporation of the solvent
  6. waitleft an oil, which
  7. customRecrystallization from ethanol (75 ml)
  8. customgave yellow-tan crystals, m.p. 100°-102° C. (11.2 g, 73% yield)

Sources & evidence

ORD record
ord-f829509b17d44c1cb5681fe7ad14355a
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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