Heptane → HCID 17384067, compound

HRID 1954775Notes

Reaction equation

HRID 1954775 reaction equation
[C:1]1([CH3:10])[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].CCCCCCC>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH:15][C:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])=[O:9]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 666492-FluorobenzylamineHCID 691942-Tolyl isocyanate

Product 1

HCID 17384067HCID 17384067, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

ortho-Tolylisocyanate (4.95 ml) was added to a solution of 2-fluorobenzylamine (4.56 ml) in toluene (50 ml) under an atmosphere of nitrogen at 5° C. to produce rapid formation of a white solid. Heptane was added, the solid broken up and filtered off to afford 1-(2-fluorobenzyl)-3-(2-methylphenyl)urea (9.5 g) as a white solid. The urea (8 g) and cyanoacetic acid (2.9 g) were ground together and heated in acetic anhydride (15 ml) to 80° C. After cooling the reaction mixture to room temperature, diethyl ether was added and washed with water. The separated ether phase was dried over magnesium sulphate, filtered and evaporated in vacuo to give a crude solid residue (8.9 g). This residue was redissolved in dichloromethane (120 ml), triethylamine (5.7 ml) added and the mixture stirred at room temperature for 3 days. Filtration of the precipitate yielded the desired uracil as a white solid (2.6 g).

Workup

  1. customto produce rapid formation of a white solid
  2. filtrationfiltered off

Sources & evidence

ORD record
ord-9cdd0bcdec1a4715b6af8abab23e5871
Source dataset
uspto-grants-2000_09
Patent number
US06124288

Reaction notes

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