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

HRID 1376100Notes

Reaction equation

HRID 1376100 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-77e186e706b142449c8a34976fca0ace
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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