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

HRID 326333노트

반응식

HRID 326333 반응식
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]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 13226857Ethyl 5-amino-2-chlorobenzoateHCID 214702502-Ethyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

생성물 1

HCID 465810Ethyl 2-chloro-5-[(6-ethyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate수율 58%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매2회

반응 조건

온도
35 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-49e93c7e7f824611b36fe9524466451f
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268389

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