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

HRID 2284543Notes

Reaction equation

HRID 2284543 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6e00f57d6d034699bd19fb25392f0114
Source dataset
uspto-grants-2015_09
Patent number
US09145438B2

Reaction notes

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