Ammonia → HCID 21487717, compound

HRID 1076582Notes

Reaction equation

HRID 1076582 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][CH:9]=[C:10]([CH3:11])[C:6]=2[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[N:4][C:3]1=[O:19].S(Cl)([Cl:23])(=O)=O.N>C(O)(=O)C>[CH3:1][N:2]1[C:7]2[S:8][C:9]([Cl:23])=[C:10]([CH3:11])[C:6]=2[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[N:4][C:3]1=[O:19]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24648Sulfuryl chlorideHCID 21487728HCID 21487728, compound

Product 1

HCID 21487717HCID 21487717, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 500 mg of 1-methyl-4-(o-fluorophenyl)-5-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one in 15 ml of glacial acetic acid is added 295 mg of sulfuryl chloride in 3 ml of glacial acetic acid at 40°C. After stirring the reaction mixture for 19 hours at room temperature, the reaction mixture is neutralized with aqueous ammonia under cooling, then extracted with chloroform. The chloroform extracts are washed with water, dried, and evaporated under reduced pressure to a residue to give crystals of 1-methyl-4-(o-fluorophenyl)-5-methyl-6-chloro-1,2-dihydrothieno[2,3-d]pyrimidin-2-one, which are recrystallized from ethanol-ether to give crystals having a melting point of 175° - 176°C.

Workup

  1. temperatureunder cooling
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with water
  4. customdried
  5. customevaporated under reduced pressure to a residue

Sources & evidence

ORD record
ord-30b77b2bee0b4ab2a8de9051ca396cc0
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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