Ethanol → HCID 19071293, compound

HRID 1955638Notes

Reaction equation

HRID 1955638 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([NH:9][CH2:10][CH2:11][CH3:12])=[O:8])=[O:5])#[N:2].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:2][C:1]1[N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[N:6]([CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:4](=[O:5])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 19071317HCID 19071317, compound

Product 1

HCID 19071293HCID 19071293, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 1-(2-cyanoacetyl)-1-cyclohexylmethyl-3-propylurea from above (7.10 g, 26.8 mmol) in water (45 mL)-ethanol (15 mL) was heated to 100° C. (oil bath), with adjustment of the pH to 10 by the addition of solid sodium carbonate. The resulting yellow solution was stirred for 1 h, during which time white crystalline solids formed. After 1 h 40 min, the mixture was cooled to 0° C. (icebath), and the white crystals were filtered off, washed with water (3×15 mL), and air-dried to provide 6-amino-3-(cyclohexylmethyl)-1-propyluracil as a slightly moist crystalline solid (8.85 g, quantitative yield). A small portion of this material was dried at 0.1 Torr to provide an analytically pure sample, m.p. 121°-122° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. customformed
  2. waitAfter 1 h 40 min
  3. filtrationthe white crystals were filtered off
  4. washwashed with water (3×15 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-6fea51d604c34e06860ff5b9ecc71c2b
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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