Propyl isocyanate → HCID 19071293, compound

HRID 1955637Notes

Reaction equation

HRID 1955637 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[C:7]([CH2:9][C:10]([NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])#[N:8]>C1(C)C=CC=CC=1>[NH2:8][C:7]1[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:6])[N:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10](=[O:11])[CH:9]=1.[C:7]([CH2:9][C:5]([N:4]([CH2:1][CH:2]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:3]1)[C:10]([NH:12][CH2:13][CH2:14][CH3:15])=[O:11])=[O:6])#[N:8]

Participants

5

Reactant 2

HCID 61033Propyl isocyanateHCID 190713252-cyano-N-(cyclohexylmethyl)acetamide

Product 2

HCID 19071293HCID 19071293, compoundHCID 19071317HCID 19071317, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Amino-3-(cyclohexylmethyl)-1-propyluracil was prepared by the method of V. Papesh, J. Org. Chem. 1951, 16, 1879-1889. A solution of propyl isocyanate (Aldrich, 10.92 mL, 116.5 mmol) and 2-cyano-N-(cyclohexylmethyl)acetamide (from step (a), 14.00 g, 77.7 mmol) in anhydrous toluene (100 mL) was stirred at reflux (heating mantle) under nitrogen for 24 h. Volatiles were then removed at 20 Torr and 50° C., and the resulting orange oil was chromatographed on silica gel. 1-(2-Cyanoacetyl)-1-cyclohexylmethyl-3-propylurea eluted with hexane/ethyl acetate (5:2) as a yellow oil, which solidified upon standing (2.708 g). Unreacted 2-cyano-N-(cyclohexylmethyl)acetamide eluted with hexane/ethylacetate (1:1) as a white crystalline solid (12.02 g), which was resubmitted to the reaction conditions described above. This process was repeated twice to provide 1-(2-cyanoacetyl)-1-cyclohexylmethyl-3-propylurea (total for the three runs: 7.101 g, 34%), 1H-NMR (DMSO-d6) consistent with structure. Unreacted 2-cyano-N-(cyclohexylmethyl)acetamide was also recovered (7.108 g, 51%).

Workup

  1. temperatureat reflux
  2. temperature(heating mantle) under nitrogen for 24 h
  3. customVolatiles were then removed at 20 Torr and 50° C.
  4. customthe resulting orange oil was chromatographed on silica gel
  5. wash1-(2-Cyanoacetyl)-1-cyclohexylmethyl-3-propylurea eluted with hexane/ethyl acetate (5:2) as a yellow oil, which
  6. washUnreacted 2-cyano-N-(cyclohexylmethyl)acetamide eluted with hexane/ethylacetate (1:1) as a white crystalline solid (12.02 g), which
  7. customwas resubmitted to the reaction conditions

Sources & evidence

ORD record
ord-b72d9e9bb3364bf3aa88ac5b8395b266
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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