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

HRID 1090615노트

반응식

HRID 1090615 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Dicyclohexylcarbodiimide (11.0Sg) was added in portions to a cooled, stirred mixture of 3-chloro-α-hydroxybenzeneacetic acid (10g), 1,1-dimethylethanamine (3.92g, 5.63ml) and 1-hydroxybenzotriazole (7.24g) in dry dimethylformamide (100ml). The mixture was stirred at ambient temperature for 20h., 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, 1.71g, as an oil which crystallized on standing, m.p. 93-99° C.

후처리

  1. stirringThe mixture was stirred at ambient temperature for 20h.
  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

출처 및 근거

ORD 기록
ord-66928f118db84009b25d33cb29173b2d
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082840

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