Water → HCID 131718035, compound

HRID 2253591Notes

Reaction equation

HRID 2253591 reaction equation
[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[NH:17][C:16]2=[O:27])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[CH3:28]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([C:23]([F:24])([F:25])[F:26])[N:17]([CH3:28])[C:16]2=[O:27])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 131718036HCID 131718036, compound

Product 1

HCID 131718035HCID 131718035, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

29,6 g of 3-[6-fluoro-2-oxo-3-(2-propinyl)-5-benzothiazolinyl]-5-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindion in 200 ml acetonitrile is stirred with 9,25 g dimethylsulfate and 10,14 g potassium carbonate at 40° C. for 90 minutes. Thereafter, the reaction mixture is poured into 200 ml of water and extracted two times with 200 ml ethyl acetate each time. The organic phase is subsequently concentrated. The thus-obtained residue is purified by chromatography with 400 g silica gel using hexane:ethyl acetate (7:3).

Workup

  1. extractionextracted two times with 200 ml ethyl acetate each time
  2. concentrationThe organic phase is subsequently concentrated
  3. customThe thus-obtained residue is purified by chromatography with 400 g silica gel

Sources & evidence

ORD record
ord-09724a5ce4f644028014dc0075583f35
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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