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

HRID 974092

反応式

HRID 974092 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 221249Butyl methylcarbamate

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9880c9027cf94417a87cd63528fcf8be
出典データセット
uspto-grants-1991_11
特許番号
US05066819

関連ノート

読み込み中…