Carbamic acid, N-methyl-, ethyl ester → Butyl methylcarbamate

HRID 974092

반응식

HRID 974092 반응식
[CH2:1]([C:5]1C=CC=C[C:6]=1[OH:11])[CH2:2]CC.[CH3:12][NH:13][C:14](=O)[O:15]CC.P(Cl)(Cl)(Cl)=O>C(Cl)CCl>[CH3:12][NH:13][C:14](=[O:15])[O:11][CH2:6][CH2:5][CH2:1][CH3:2]

참가 물질

5

반응물 3

HCID 7752Carbamic acid, N-methyl-, ethyl esterHCID 185152-ButylphenolHCID 24813Phosphorus oxychloride

생성물 1

HCID 221249Butyl methylcarbamate

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) in ethylene dichloride (6 ml) was added phosphoryl chloride (0.77 g, 0.05 mole) and the reaction mixture was refluxed under stirring for twenty hours. It was poured onto ice-cold water. The organic layer separated and aqueous layer was extracted with dichloroethane. The combined organic layer was washed with water, dried (Na2SO4) and distilled to give liquid residue, which was further purified by distillation to give 2-sec butyl N-methylcarbamate of the formula (III) [96% by GLC, DV-101 (3%), 150° C., nitrogen, 30 ml/min.] as a liquid, b.p. 110° C. (vap.)/4 mm; IR: 3320 (N--H), 1730 (--COO--), 1535,1490 and 750 (aromatic); PMR (CDCl3, 90 MHz): 0.81 (3H,t, primary methyl of side chain, 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH--CH3 and benzylic proton), 4.97 (1H, br s, N--H) and 6.95 to 7.25 (4H, m, aromatic).

후처리

  1. temperaturethe reaction mixture was refluxed
  2. additionIt was poured onto ice-cold water
  3. customThe organic layer separated
  4. extractionaqueous layer was extracted with dichloroethane
  5. washThe combined organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. distillationdistilled
  8. customto give liquid residue, which
  9. distillationwas further purified by distillation

출처 및 근거

ORD 기록
ord-9880c9027cf94417a87cd63528fcf8be
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066819

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