Thionyl Chloride → 5-Methyl-4-oxo-1,4-dihydrothieno[2,3-d]pyrimidine-6-sulfonyl chloride

HRID 450586Notes

Reaction equation

HRID 450586 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14].S(Cl)(Cl)=O>>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[S:13]([Cl:12])(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 2902265-methyl-3H,4H-thieno[2,3-d]pyrimidin-4-one

Product 1

HCID 866656665-Methyl-4-oxo-1,4-dihydrothieno[2,3-d]pyrimidine-6-sulfonyl chloride

Procedure

5-Methylthieno[2,3-d]pyrimidin-4(3H)-one (2 g, 12 mmol) was added portionwise into chlorosulfonic acid (8.0 mL, 120 mmol) maintaining the internal temperature below 0° C. After addition the reaction was stirred for 10 minutes, thionyl chloride (4.4 mL, 60 mmol) added drop wise, the mixture stirred for 0.5 hours at ambient temperature and then at reflux for 2 hours. The solution was poured onto crushed ice, the precipitated solid collected by filtration, washed with ice-water, and dried under vacuum to give cream solid. (1.1 g, 34%).

Workup

  1. temperaturemaintaining the internal temperature below 0° C
  2. additionAfter addition the reaction
  3. stirringthe mixture stirred for 0.5 hours at ambient temperature
  4. temperatureat reflux for 2 hours
  5. additionThe solution was poured
  6. customonto crushed ice
  7. filtrationthe precipitated solid collected by filtration
  8. washwashed with ice-water
  9. customdried under vacuum
  10. customto give cream solid

Sources & evidence

ORD record
ord-a5a62a7a3201406d844303ab26974bfc
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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