Methylamine → 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carboxamide

HRID 264838노트

반응식

HRID 264838 반응식
[F:1][CH2:2][C:3]1([CH2:19][F:20])[CH:8]=[C:7]([C:9](O)=[O:10])[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.CN.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][CH2:2][C:3]1([CH2:19][F:20])[CH:8]=[C:7]([C:9]([NH:23][CH3:21])=[O:10])[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 211949872,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carboxylic acid

생성물 1

HCID 190370412,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carboxamide수율 15.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 0.78 g of 2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxylic acid and 5 ml of tetrahydrofuran was added 0.67 g of 1,1'-carbonyldiimidazole with stirring under ice-cooling and the mixture was stirred for 1 hour. Then, 6.3 ml of 40% methylamine (methanol solution) was added therein. The resultant mixture was stirred under ice-cooling for 1 hour and then at room temperature for 14 hours. An aqueous potassium carbonate solution was added therein and the mixture was extracted with ether. An organic layer was washed with water and dried, and the solvent was distilled. The obtained residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.13 g of 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carboxamide with a melting point of 178°-179° C.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hour
  3. temperaturecooling for 1 hour
  4. extractionthe mixture was extracted with ether
  5. washAn organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled
  8. customThe obtained residue was purified

출처 및 근거

ORD 기록
ord-c5d156e79f4c4534b588cc877d04b46f
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646308

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