Dimethylformamide → 4-Isopropyl-6-methoxy-2-saccharinylmethyl thiophene-3-carboxylate

HRID 864759Notes

Reaction equation

HRID 864759 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.Cl[CH2:21][N:22]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][C:28]([O:37][CH3:38])=[CH:29][C:30]=2[CH:34]([CH3:36])[CH3:35])[S:23]1(=[O:25])=[O:24]>O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:21][N:22]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][C:28]([O:37][CH3:38])=[CH:29][C:30]=3[CH:34]([CH3:36])[CH3:35])[S:23]2(=[O:24])=[O:25])=[O:7])=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6918Thiophene-3-carboxylic acidHCID 11430Potassium CarbonateHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 152255224-Isopropyl-6-methoxy-2-saccharinylmethyl thiophene-3-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-thiophene carboxylic acid (0.26 g, 2.0 mmol), K2CO3 (0.28 g, 2.0 mmol) and DMF (4 ml) was stirred for 1 hour. 2-Chloromethyl-4-isopropyl-6-methoxy-saccharin (0.61 g, 2.0 mmol) was then added and the mixture was stirred for 24 hours. Water (20 ml) was added to the reaction mixture and the solution was extracted with ether (2×40 ml). The organic layer was separated, washed with water, then brine and was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the solid residue was recrystallized from toluene/hexane to afford 0.5 g (65%) of 4-isopropyl-6-methoxy-2-saccharinylmethyl thiophene-3-carboxylate as a white powder, m.p. 125°-127° C.

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. extractionthe solution was extracted with ether (2×40 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine and was dried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe solid residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-7d0bd053941c4d65b534cde3daf05190
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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