Sodium Acetate → HCID 14653255, compound

HRID 893308Notes

Reaction equation

HRID 893308 reaction equation
Br[CH2:2][C:3]1[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5](=[O:16])[C:6]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:9][C:7]=2[N:8]=1.[C:24]([O-:27])(=[O:26])[CH3:25].[Na+]>CN(C)C=O>[C:24]([O:27][CH2:2][C:3]1[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5](=[O:16])[C:6]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:9][C:7]=2[N:8]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14653254HCID 14653254, compound

Product 1

HCID 14653255HCID 14653255, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 10.5 g of 3,4-dihydro-2-bromomethyl-3-(2-chlorophenyl)-4-oxo-6-sulfamoylthieno[2,3-d]pyrimidine were added 100 ml of dimethylformamide and 6.0 g of sodium acetate, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was poured onto water, and the mixture was extracted with ethyl acetate, washed with water and concentrated to give 8.7 g of the residue. This residue was purified by silica gel column chromatography to give 5.3 g of an oily substance, which was crystallized from ethanol to afford 3.4 g of the title compound, m.p. 192.5°-194° C.

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d8d1395ddbb46eb9a941d3d58debf0d
Source dataset
uspto-grants-1992_06
Patent number
US05124331

Reaction notes

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