4-tert-Butylbenzoic acid → Benzoic acid, 4-(1,1-dimethylethyl)-, hydrazide

HRID 393828

반응식

HRID 393828 반응식
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:29][NH2:30]>C(OCC)(=O)C>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:29][NH2:30])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 74034-tert-Butylbenzoic acidHCID 79724-MethylmorpholineHCID 9321HydrazineHCID 62365Isobutyl chloroformate

생성물 1

HCID 123513Benzoic acid, 4-(1,1-dimethylethyl)-, hydrazide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

A solution of 4-tert-butyl benzoic acid (0.2 g, 1.2 mmol in 10 mL of dry THF) cooled to 0° C. and treated with N-methyl-morpholine (1.6 mL, 14.6 mmol) as well as isobutyl chloroformate (1.7 mL, 1.3 mmol). Then the mixture was stirred for 10 minutes at 0° C. After hydrazine (0.6 g, 3.6 mmol) was added to the reaction mixture, it was stirred 3 hours at 25° C. The reaction was then diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate solution as well as brine, and concentrated in vacuum. The crude material was chromatographed on silica gel eluting with hexanes/ethyl acetate=2:1 to give 4-tert-butyl-benzoic acid hydrazide.

후처리

  1. stirringwas stirred 3 hours at 25° C
  2. washwashed with saturated sodium bicarbonate solution as well as brine
  3. concentrationconcentrated in vacuum
  4. customThe crude material was chromatographed on silica gel eluting with hexanes/ethyl acetate=2:1

출처 및 근거

ORD 기록
ord-f8af978295af440990998aaf3a31624f
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809119B2

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