Pyridine → HCID 10497271, compound

HRID 615146Notes

Reaction equation

HRID 615146 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([N:22]=[C:23]=[O:24])[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].N1C=CC=CC=1>ClCCl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:22][C:23]([N:6]2[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]2=[O:8])=[O:24])[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 33855-FluorouracilHCID 5177665-Isocyanato-1,2,3-trimethoxybenzene

Product 1

HCID 10497271HCID 10497271, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3.9 g of 5-fluorouracil, 6.27 g of 3, 4, 5-trimethoxyphenylisocyanate and 15 ml of pyridine was heated at 90° C. for 2 hr and, after evaporating pyridine, 100 ml of dichloromethane and 200 ml of hydrochloric acid water were added to it. The insoluble substance produced was combined with the substance dissolved in the dichloromethane. The combined substances were washed with water and then with ethanol, and 4.8 g of 1-(3, 4, 5-trimethoxyphenylcarbamoy)-5-fluorouracil (melting point: 168°-170° C.) was obtained (Compound No. 6). NMR: 3.76 (3H s OCH3) 3.84 (6H s OCH3) 6.64-7.0 (2H b C6H2).

Workup

  1. customafter evaporating pyridine, 100 ml of dichloromethane and 200 ml of hydrochloric acid water
  2. additionwere added to it
  3. customThe insoluble substance produced
  4. washThe combined substances were washed with water

Sources & evidence

ORD record
ord-ab67e4ab0ed64bf9a7b537de97bb71fd
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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