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

HRID 1376100ノート

反応式

HRID 1376100 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 167703662-Amino-N-tert-butyl-5-chlorobenzamide収率 76.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77e186e706b142449c8a34976fca0ace
出典データセット
uspto-grants-2007_01
特許番号
US07169925B2

反応ノート

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