Dimethylformamide → HCID 20033726, compound

HRID 231677Notes

Reaction equation

HRID 231677 reaction equation
[K].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[S:15][C:14]([S:16](O)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:6]([F:20])[CH:5]=1)#[N:3].C(Cl)(=O)C(Cl)=O.C[N:28](C=O)C>C(OCC)(=O)C.[Cl-].[Na+].O>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[S:15][C:14]([S:16]([NH2:28])(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:6]([F:20])[CH:5]=1)#[N:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5462222PotassiumHCID 20033732HCID 20033732, compound

Product 1

HCID 20033726HCID 20033726, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The potassium salt of 5-[4-cyano-2-fluorophenylthio]thiophene-2-sulfonic acid (11.70 g, 33.12 mmol) was suspended in ethyl acetate and oxalyl chloride (8.41 g, 66.23 mmol) then cooled to -50° C., DMF (1.21 g, 16.56 mmol) was added dropwise and stirring at room temperature was continued overnight. The mixture was then cautiously diluted with 150 ml of brine. After washing the organic layer with H2O, 50 ml of concentrated NH4OH was added and the mixture was stirred for 2 hours. The solution was made acidic with HCl and diluted with water. The layers were separated and the organic phase was dried over MgSO4, filtered and concentrated to dryness to give 4.83 g of solid.

Workup

  1. washAfter washing the organic layer with H2O, 50 ml of concentrated NH4OH
  2. additionwas added
  3. stirringthe mixture was stirred for 2 hours
  4. additiondiluted with water
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-67c92519a0284f5cbc00154678c4fdc1
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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