Triethylamine → HCID 465809, compound

HRID 1938845Notes

Reaction equation

HRID 1938845 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:25]=[CH:26][CH:27]=1)[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].C(N(CC)CC)C>C(Cl)Cl.C(O)C>[CH3:5][C:6]1[O:7][CH2:8][CH2:9][S:10][C:11]=1[C:12]([NH:15][C:16]1[CH:27]=[CH:26][CH:25]=[C:18]([CH:17]=1)[C:19]([O:21][CH:22]([CH3:23])[CH3:24])=[O:20])=[O:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 236743isopropyl 3-aminobenzoateHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

Product 1

HCID 465809HCID 465809, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (3.5 g, 0.029 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (4.7 g, 0.029 mole) and methylene chloride (100 ml). The mixture was warmed to 30°-35° C. for 4 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 1-methylethyl 3-aminobenzoate (5,.2 g, 0.029 mole) and triethylamine (2.9 g, 0.029 mole) in methylene chloride (50 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 left an oil, which solidified. After recrystallization from ethanol (30 ml) the product (4.0 g, 42% yield) melted at 92°-94° C.

Workup

  1. temperatureThe mixture was warmed to 30°-35° C. for 4 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. waitleft an oil, which

Sources & evidence

ORD record
ord-90e45774744b44b68e872e5d0e88e619
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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