Triethylamine → Ethyl 2-chloro-5-[(6-ethyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate

HRID 326333Notes

Reaction equation

S(Cl)(Cl)=O.[CH2:5]([C:7]1[O:8][CH2:9][CH2:10][S:11][C:12]=1[C:13]([OH:15])=O)[CH3:6].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:28])=[C:21]([CH:27]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(Cl)Cl.C(O)C>[Cl:28][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:13]([C:12]2[S:11][CH2:10][CH2:9][O:8][C:7]=2[CH2:5][CH3:6])=[O:15])=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Conditions

Temperature: 35 °C

Procedure

Thionyl chloride (4.0 g, 0.034 mole) was added to a stirred mixture of 2-ethyl-5,6-dihydro-1,4-oxathiin-3-carboxylic acid (5.9 g, 0.034 mole) and methylene chloride (100 ml). The mixture was warmed to about 35° C. for 3 hours, then evaporated under reduced pressure. The residue, crude 2-ethyl-5,6-dihydro-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 5-amino-2-chlorobenzoate (6.8 g, 0.034 mole) and triethylamine (3.7 g, 0.037 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 left an oil, which solidified. After recrystallization from ethanol (30 ml) the product (7.0 g, 58% yield) melted at 86°-88° C.

Workup

customevaporated under reduced pressure
dissolutionThe residue, crude 2-ethyl-5,6-dihydro-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml)
temperaturethe ice-chilled solution
washby washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water
customEvaporation of the solvent
waitleft an oil, which

Sources & evidence

ORD record: ord-49e93c7e7f824611b36fe9524466451f
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268389

Reaction notes

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