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

HRID 920919Notes

Reaction equation

HRID 920919 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:32][C:33]([NH2:36])([CH3:35])[CH3:34]>C1COCC1>[C:33]([NH:36][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])([CH3:35])([CH3:34])[CH3:32]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 83742-Chlorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 4644665N-tert-butyl-2-chlorobenzamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-chlorobenzoic acid (20 g, 128 mmol), HOBT (34.6 g, 256 mmol), EDCI (48.8 g, 256 mmol), 2-methylpropan-2-amine (9.3 g, 128 mmol) and TEA (25.9 g, 256 mmol) in THF (600 mL) was stirred at room temperature overnight. After solvent evaporation, the mixture was diluted with ethyl acetate (600 mL) and washed with water (3×300 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/PE (1:5) to give the title product as a white solid (23.9 g, yield: 88.5%). LC-MS: m/e=212 (M+H)+; Rt=0.85 min.

Workup

  1. customAfter solvent evaporation
  2. additionthe mixture was diluted with ethyl acetate (600 mL)
  3. washwashed with water (3×300 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/PE (1:5)

Sources & evidence

ORD record
ord-bf160d1d6d0c412abd21f08251013330
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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