Water → HCID 19745811, compound

HRID 2253584Notes

Reaction equation

HRID 2253584 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([C:10]2[C:11]([F:20])=[CH:12][C:13]3[S:17][C:16](=[O:18])[NH:15][C:14]=3[CH:19]=2)[C:3]1=[O:21].[H-].[Na+].Cl[CH2:25][C:26]([NH2:28])=[O:27].O>CN(C)C=O>[C:26]([CH2:25][N:15]1[C:14]2[CH:19]=[C:10]([N:4]3[C:5](=[O:9])[CH:6]=[C:7]([CH3:8])[N:2]([CH3:1])[C:3]3=[O:21])[C:11]([F:20])=[CH:12][C:13]=2[S:17][C:16]1=[O:18])(=[O:27])[NH2:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 19745785HCID 19745785, compound

Product 1

HCID 19745811HCID 19745811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3.07 g of 1,6-dimethyl-3-(6-fluoro-2-oxo-5-benzothiazolinyl)-2,4(1H,3H)-pyrimidinedione (see Example 79) and 0.48 g of a 55% sodium hydride dispersion are stirred at 25° C. for 1 hour in 50 ml of absolute dimethylformamide. Subsequently, 1.02 g of chloroacetamide are added and the mixture is stirred at 50° C. for 6 hours. The reaction mixture is cooled and treated with 400 ml of water. The precipitated product is filtered off under suction, washed with water and the filter cake is suspended in 200 ml of ethyl acetate at 60° C. The suspension is concentrated to about 50 ml, cooled to 25° C., the solid is filtered off under suction and dried at 50° C. In this manner there is obtained 3-(3-carbamoylmethyl-6-fluoro-2-oxo-5-benzothiazolinyl)-1,6-dimethyl-2,4(1H,3H)-pyrimidinedione, m.p.>260° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe precipitated product is filtered off under suction
  3. washwashed with water
  4. customis suspended in 200 ml of ethyl acetate at 60° C
  5. concentrationThe suspension is concentrated to about 50 ml
  6. temperaturecooled to 25° C.
  7. filtrationthe solid is filtered off under suction
  8. customdried at 50° C

Sources & evidence

ORD record
ord-0fe2bb61cd3c4a83b40d5a09411e0092
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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