Water → 4'-Methyl-[1,1'-biphenyl]-4-carbohydrazonamide

HRID 923576노트

반응식

HRID 923576 반응식
[NH2:1][NH2:2].C([Li])CCC.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.O>C1COCC1>[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[N:1][NH2:2])[NH2:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 9321HydrazineHCID 170889(1,1'-Biphenyl)-4-carbonitrile, 4'-methyl-HCID 178418339Butyllithium

생성물 1

HCID 68606274'-Methyl-[1,1'-biphenyl]-4-carbohydrazonamide수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirring solution of hydrazine (3.32 mL, 3.32 mmol, 1 M in THF) in THF (5 mL) at −78° C. was added butyllithium (1.28 mL, 3.05 mmol, 2.5 M in hexanes). After 30 min, a solution of 4′-methyl-[1,1′-biphenyl]-4-carbonitrile (535 mg, 2.77 mmol) in THF (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto water (150 mL) and stirred vigorously for 1 h. The precipitate was isolated by filtration using water (2×20 mL) and isohexanes (3×20 mL) to wash the filter cake. The solid was dried under vacuum to yield 560 mg (90%) of 4′-methyl-[1,1′-biphenyl]-4-carbohydrazonamide INT-39 as a fine yellow solid. LCMS-ESI (m/z) calculated for C14H15N3: 225; found 226 [M+H]+, tR=1.15 min (Method 10).

후처리

  1. additionThe reaction mixture was poured onto water (150 mL)
  2. stirringstirred vigorously for 1 h
  3. customThe precipitate was isolated by filtration
  4. washto wash the filter cake
  5. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-18ffef9c792c4b20a3e880c989f76363
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278910B2

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