Oxalyl chloride → 2-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide

HRID 1753720

반응식

HRID 1753720 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.[CH3:8][O:9][C:10]1[C:18]([S:19][CH3:20])=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[CH3:8][O:9][C:10]1[C:18]([S:19][CH3:20])=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=[CH:15][C:11]=1[C:12]([NH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1)=[O:13]

참가 물질

5

반응물 3

HCID 65578Oxalyl chloride2회HCID 1384921-methyl-1H-tetrazol-5-amineHCID 669579072-Methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid

생성물 1

HCID 897687922-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide수율 46.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

1.45 g (98% by weight; 14.3 mmol) of 5-amino-1-methyl-1H-tetrazole were added to 3.00 g (11.3 mmol) of 2-methoxy-3-(methylsulfanyl)-4-(trifluoromethyl)benzoic acid in 30 ml of dry pyridine. 2.00 g (15.8 mmol) of oxalyl chloride were then added, and the mixture was subsequently stirred at room temperature (RT) for three days. Another 500 mg (3.94 mmol) of oxalyl chloride were then added, and the mixture was subsequently stirred at RT for 16 h. For work-up, the contents were substantially freed from the solvent on a rotary evaporator. The residue was stirred with dichloromethane and a saturated solution of sodium bicarbonate. The organic phases were then separated and the organic phase was freed from the solvent on a rotary evaporator. The residue was purified chromatographically, which gave 1.83 g of clean product.

후처리

  1. stirringthe mixture was subsequently stirred at RT for 16 h
  2. customFor work-up, the contents were substantially freed from the solvent on a rotary evaporator
  3. stirringThe residue was stirred with dichloromethane
  4. customThe organic phases were then separated
  5. customthe organic phase was freed from the solvent on a rotary evaporator
  6. customThe residue was purified chromatographically

출처 및 근거

ORD 기록
ord-6e42f933ffe44b92a03fe1941df17cc5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09167819B2

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