Dimethylcarbamoyl Chloride → HCID 13041531, compound

HRID 66721Notes

Reaction equation

HRID 66721 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[N:4][C:5]([C:9]([Cl:12])([Cl:11])[Cl:10])=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C(#N)C>[CH3:21][N:22]([CH3:26])[C:23](=[O:24])[O:13][C:3]1[C:2]([Cl:1])=[C:7]([CH3:8])[N:6]=[C:5]([C:9]([Cl:10])([Cl:11])[Cl:12])[N:4]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178432777HCID 178432777, compound

Product 1

HCID 13041531HCID 13041531, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.9 g (0.015 mole) 5-chloro-4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 1.6 g (0.015 mole) triethylamine, 1.7 g (0.015 mole) dimethylcarbamoyl chloride, and 80 ml acetonitrile was refluxed 3 days. Rotary evaporation to concentrate the solution yielded a precipitate that was removed by filtration. Rotary evaportation of the filtrate gave a residue which was triturated with petroleum ether to give 1.0 g (20% yield; mp 87°-88° C.) of product. The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperaturewas refluxed 3 days
  2. customRotary evaporation
  3. concentrationto concentrate the solution
  4. customyielded a precipitate that
  5. customwas removed by filtration
  6. customRotary evaportation of the filtrate gave a residue which
  7. customwas triturated with petroleum ether
  8. customto give 1.0 g (20% yield; mp 87°-88° C.) of product

Sources & evidence

ORD record
ord-f343f99435f1456ebdc3b9a082d7ff09
Source dataset
uspto-grants-1982_08
Patent number
US04343803

Reaction notes

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