Cyanuric chloride → tert-Butyl ((1-(cyanomethyl)cyclohexyl)methyl)carbamate

HRID 1795509노트

반응식

HRID 1795509 반응식
N1C(Cl)=NC(Cl)=NC=1Cl.[C:10]([O:14][C:15](=[O:28])[NH:16][CH2:17][C:18]1([CH2:24][C:25](=O)[NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:13])([CH3:12])[CH3:11].CCCCCC.CCOC(C)=O>CN(C=O)C>[C:10]([O:14][C:15](=[O:28])[NH:16][CH2:17][C:18]1([CH2:24][C:25]#[N:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)([CH3:11])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 7954Cyanuric chlorideHCID 21226206Ethyl acetate hexaneHCID 53862491(1-Carbamoylmethyl-cyclohexylmethyl)-carbamic Acid tert-butyl Ester

생성물 1

HCID 53643555tert-Butyl ((1-(cyanomethyl)cyclohexyl)methyl)carbamate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cyanuric chloride (39.5 g, 0.214 mol) was added to (1-carbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (3) (116 g, 0.429 mol) in 400 mL DMF. An ice-water bath was used to moderate the exotherm, and the reaction mixture was stirred at room temperature for 1.5 hours. The mixture was poured into ice-water containing 120 g (1.43 mol) NaHCO3 and was extracted 4×EtOAc. The extracts were washed 1×water, 2×brine and dried over Na2SO4. Evaporation yielded an oil which was taken up in 3:1 hexane/EtOAc and filtered through silica gel. Evaporation yielded white crystals (86.5 g, 80%); mp 54–58° C.

후처리

  1. customAn ice-water bath was used
  2. extractionwas extracted 4×EtOAc
  3. washThe extracts were washed 1×water, 2×brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation
  6. customyielded an oil which
  7. filtrationfiltered through silica gel
  8. customEvaporation

출처 및 근거

ORD 기록
ord-2471359e31f147a9a7375b272d4f0bd9
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026505B2

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