Thionyl Chloride → 6-Chlorosulphonylthieno[2,3-d]pyrimidin-4-one

HRID 2049027Notes

Reaction equation

HRID 2049027 reaction equation
[N:1]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.[Cl:11][S:12](O)(=[O:14])=[O:13].S(Cl)(Cl)=O>>[Cl:11][S:12]([C:8]1[S:7][C:6]2[N:1]=[CH:2][NH:3][C:4](=[O:10])[C:5]=2[CH:9]=1)(=[O:14])=[O:13]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 2808547thieno(2,3-d)pyrimidin-4(3H)-one

Product 1

HCID 203454966-Chlorosulphonylthieno[2,3-d]pyrimidin-4-one

Procedure

3,4-Dihydrothieno [2,3-d] pyrimidin-4-one (50 g) was added portionwise to chlorosulphonic acid (243 ml), maintaining the temperature below 0° C. Thionyl chloride (121 ml) was added dropwise, and the mixture stirred for a further 30 minutes at room temperature; then two hours at reflux. It was then cooled, and poured carefully on to ice. The precipitate was washed and dried to give 6-chlorosulphonylthieno[2,3-d]pyrimidin-4-one (84 g). This compound (30 g) and dimethylamine (450 ml) were mixed at -10°, then allowed to stir at room temperature for two hours. The mixture was poured into water and acidified with hydrochloric acid. The precipitate was washed with water and ethanol, and dried to give the 6-dimethylsulphonamido-4-one (23.8 g). This material was converted into the 4-chloro derivative as described in Example 19 above and thence into the title compounds by treatment with amines basically as described in Example 5.

Workup

  1. temperaturemaintaining the temperature below 0° C
  2. temperaturethen two hours at reflux
  3. temperatureIt was then cooled
  4. additionpoured carefully on to ice
  5. washThe precipitate was washed
  6. customdried

Sources & evidence

ORD record
ord-b0aba2128b6e48168733c72947b8cc58
Source dataset
uspto-grants-1980_04
Patent number
US04196207

Reaction notes

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