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

HRID 1938842

반응식

HRID 1938842 반응식
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]=[CH:18][C:19]([Cl:29])=[C:20]([CH:28]=1)[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[Cl:29][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:12]([C:11]2[S:10][CH2:9][CH2:8][O:7][C:6]=2[CH3:5])=[O:14])=[CH:28][C:20]=1[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acidHCID 21470254Butyl 5-amino-2-chlorobenzoate

생성물 1

HCID 465806Butyl 2-chloro-5-[(6-methyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate수율 41%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Thionyl chloride (4.4 g, 0.037 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (5.0 g, 0.031 mole) and methylene chloride (50 ml). The mixture was warmed to 35°-40° C. for about 3 hours, left stirring overnight at room temperature, and 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) and the solution treated dropwise at 5°-10° C. over 2 hours with a solution of butyl 5-amino-2-chlorobenzoate (6.1 g, 0.031 mole) and triethylamine (3.6 g, 0.036 mole) in methylene chloride (50 ml). The reaction mixture was stirred at room temperature for a further 3 hours and then 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 (50ml). Evaporation of the solvent left an oil, which slowly solidified. Recrystallization from methanol (50 ml) gave beige crystals, m.p. 71°-73° C. (4.7 g, 41% yield).

후처리

  1. temperatureThe mixture was warmed to 35°-40° C. for about 3 hours
  2. waitleft
  3. customevaporated under reduced pressure
  4. dissolutionThe solid residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (50 ml)
  5. stirringThe reaction mixture was stirred at room temperature for a further 3 hours
  6. 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 (50ml)
  7. customEvaporation of the solvent
  8. waitleft an oil, which
  9. customRecrystallization from methanol (50 ml)
  10. customgave beige crystals, m.p. 71°-73° C. (4.7 g, 41% yield)

출처 및 근거

ORD 기록
ord-0a8087d9780d4e799ea7084e41f1713b
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693827

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