Tert-Butylamine → N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

HRID 2072770Notes

Reaction equation

HRID 2072770 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]([OH:27])[C:24]([OH:26])=O)[CH:20]=[CH:21][CH:22]=1.[CH3:28][C:29]([CH3:32])([NH2:31])[CH3:30].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:28][C:29]([NH:31][C:24](=[O:26])[CH:23]([OH:27])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=1)([CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 859813-Chloromandelic acid

Product 1

HCID 19913633N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dicyclohexylcarbodiimide (11.05 g) was added in portions to a cooled, stirred mixture of 3-chloro-α-hydroxybenzeneacetic acid (10 g), 1,1-dimethylethanamine (3.92 g, 5.63 ml) and 1-hydroxybenzotriazole (7.24 g) in dry dimethylformamide (100 ml). The mixture was stirred at ambient temperature for 20 h., filtered and the filtrate evaporated. The residual oil was taken up in ethyl acetate, filtered, and the filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water. The organic layer was dried (MgSO4), filtered, and evaporated to an oil which was chromatographed on silica. Elution with chloroform gave N-[1,1-dimethylethyl]-3-chloro-α-hydroxybenzeneacetamide, 1.71 g, as an oil which crystallized in standing, m.p. 93°-99° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 20 h.
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. filtrationfiltered
  5. washthe filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil which
  9. customwas chromatographed on silica
  10. washElution with chloroform

Sources & evidence

ORD record
ord-1b6b7b0dc87b4406ab6a8a374b4ed882
Source dataset
uspto-grants-1990_04
Patent number
US04914202

Reaction notes

Loading…