Ethyl Acetate → 1-(4-Tert-butylphenyl)-3-(3-hydroxypropyl)urea

HRID 2284543ノート

反応式

HRID 2284543 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>C(OCC)C.C(Cl)Cl.C1(C)C=CC=CC=1>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:18])=[CH:12][CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 90863-Amino-1-propanolHCID 27356951-Tert-butyl-4-isocyanatobenzene

生成物 1

HCID 535206861-(4-Tert-butylphenyl)-3-(3-hydroxypropyl)urea収率 110%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-amino-1-propanol (0.180 mL, 2.36 mmol) in diethylether (15 mL) was cooled at 0° C. and treated dropwise with 1-tert-butyl-4-isocyanatobenzene (0.400 mL, 2.25 mmol). The reaction mixture was allowed to slowly warm to room temperature. After 16 h the reaction was found to be complete by TLC (100% ethyl acetate) The reaction mixture was diluted with 10 mL portions of CH2Cl2 and Et2O and washed with 15 mL portions of H2O, 0.5N HCl and brine and dried over Na2SO4. The organic phase was filtered and concentrated to yield a colorless viscous oil which was dissolved in PhCH3, concentrated and placed under high vac overnight to yield the title compound (600 mg, 110%) as a colorless viscous oil: MS (ESI+) for C14H22N2O2 m/z 251.0 (M+H)+; (ESI−) for C14H22N2O2 m/z 249.3 (M−H)−; HPLC purity 98% (ret. time, 3.43 min).

後処理

  1. washwashed with 15 mL portions of H2O, 0.5N HCl and brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe organic phase was filtered
  4. concentrationconcentrated
  5. customto yield a colorless viscous oil which
  6. concentrationconcentrated
  7. waitplaced under high vac overnight

出典と根拠

ORDレコード
ord-6e00f57d6d034699bd19fb25392f0114
出典データセット
uspto-grants-2015_09
特許番号
US09145438B2

反応ノート

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