Chlorosulfonic acid → 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride

HRID 1721864Notes

Reaction equation

HRID 1721864 reaction equation
[CH3:1][N:2]1[CH:9]=[CH:8][C:6](=[O:7])[N:5]([CH3:10])[C:3]1=[O:4].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[CH3:1][N:2]1[CH:9]=[C:8]([S:12]([Cl:11])(=[O:14])=[O:13])[C:6](=[O:7])[N:5]([CH3:10])[C:3]1=[O:4]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 701221,3-Dimethyluracil

Product 1

HCID 49627171,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chlorideYield 79.2%

Procedure

1,3-Dimethyluracil (411 g, 2.93M) was added portionwise over 30 minutes to chlorosulfonic acid (5480 g, 47.0M) with stirring at room temperature. The exotherm was allowed to proceed to 50° C. without cooling. Upon completion of addition, the reaction was heated gradually to reflux (~154° C.) for 2 hours. Upon cooling the reaction was cautiously poured onto ice. The resultant solid was filtered off, washed thoroughly with water and dried in vacuo at 40° C. for 16 hours. An off-white solid (554 g, 79.2%), m.p. 225°-230° C. (dec.) was obtained.

Workup

  1. customto proceed to 50° C.
  2. temperaturewithout cooling
  3. additionUpon completion of addition
  4. temperaturethe reaction was heated gradually
  5. temperatureto reflux (~154° C.) for 2 hours
  6. temperatureUpon cooling the reaction
  7. additionwas cautiously poured onto ice
  8. filtrationThe resultant solid was filtered off
  9. washwashed thoroughly with water
  10. customdried in vacuo at 40° C. for 16 hours

Sources & evidence

ORD record
ord-2883fe6d9cac4aaeb2d139b0c7533969
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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