Dimethylformamide → HCID 15007574, compound

HRID 1770080Notes

Reaction equation

HRID 1770080 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O:11]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15](S(C)(=O)=O)[N:14]=1)[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:11]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([S:1][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[N:14]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 178524460HCID 178524460, compound

Product 1

HCID 15007574HCID 15007574, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4.0 g (0.026 mol) of 2-mercaptonicotinic acid, 5.7 g (0.026 mol) of 4,6-dimethoxyl-2-methylsulfonylpyrimidine and 7.2 g (0.052 mol) of potassium carbonate were weighed, and 70 ml of dimethylformamide was added thereto and the mixture was stirred at 80° C. for 2 hours. The resultant mixture was poured into water, and was washed with 100 ml of ethyl acetate. The aqueous layer was then acidified with 10% HCl aqueous solution to precipitate a crystal. The crystal thus precipitated was filtrated out, and was washed with water and was dried. The crystal was then recrystallized with methanol to obtain 5.3 g of a light-yellowish crystal of the aimed product.

Workup

  1. washwas washed with 100 ml of ethyl acetate
  2. customto precipitate a crystal
  3. customThe crystal thus precipitated
  4. filtrationwas filtrated out
  5. washwas washed with water
  6. customwas dried
  7. customThe crystal was then recrystallized with methanol

Sources & evidence

ORD record
ord-8bb85bb18ffe4ba9aad4072b4f3203be
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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