Tert-Butylamine → 2-Amino-N-tert-butyl-5-chlorobenzamide

HRID 1376100노트

반응식

HRID 1376100 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36]>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:6]

참가 물질

6

반응물 4

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 124762-Amino-5-chlorobenzoic acidHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 167703662-Amino-N-tert-butyl-5-chlorobenzamide수율 76.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Stir and cool to 0° C. a solution of 2-amino-5-chlorobenzoic acid (1.21 g, 10 mmol) and N-hydroxysuccinimide (1.38 g, 12 mmol) in dichloromethane (12 mL). Add, dropwise, a 1M solution of dicyclohexylcarbodiimide in dichloromethane (12 mL, 12 mmol), and stir at 0° C. for 1 h. Add tert-butyl amine (1.74 g, 23.79 mmol) by syringe and stir at ambient temperature overnight. Filter the reaction mixture and wash the filtrate with aqueous sodium bicarbonate. Dry the organic phase with MgSO4 and chromatograph over silica gel eluting with 4% ethyl acetate/dichloromethane to afford 1.74 g of the title compound: MS 227(M+H), m.p. 126–127° C.

후처리

  1. additionAdd
  2. filtrationFilter the reaction mixture
  3. washwash the filtrate with aqueous sodium bicarbonate
  4. dry with materialDry the organic phase with MgSO4 and chromatograph over silica gel eluting with 4% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-77e186e706b142449c8a34976fca0ace
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169925B2

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