Water → 1-Methyl-3-cyclohexyl-6-chlorouracil

HRID 65911Notes

Reaction equation

HRID 65911 reaction equation
[CH3:1][N:2]1[C:9](=O)[CH2:8][C:6](=[O:7])[N:5]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]1=[O:4].O.P(Cl)(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:9]([Cl:20])=[CH:8][C:6](=[O:7])[N:5]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 127685551-Methyl-3-cyclohexylbarbituric acid

Product 1

HCID 123805901-Methyl-3-cyclohexyl-6-chlorouracil

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

35 g of 1-methyl-3-cyclohexylbarbituric acid is admixed with 15 ml of water and, then, 150 ml of phosphorus oxychloride is added. The reaction mixture is boiled for 1 hour, after which it is poured in ice-water, whereupon 35 g (dry weight) of yellow crystals are obtained. The crystals are dissolved in a small amount of chloroform and chromatographed on a column of silica gel (400 g). The first fraction is collected and concentrated to dryness. By the above procedure is obtained 14 g of 1-methyl-3-cyclohexyl-6-chlorouracil as colorless crystals, melting point: 132°-133° C.

Workup

  1. customare obtained
  2. customchromatographed on a column of silica gel (400 g)
  3. customThe first fraction is collected
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9d749d69980c462d9550dbc80ab1ec7f
Source dataset
uspto-grants-1978_12
Patent number
US04129654

Reaction notes

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