Sulfuric Acid → HCID 19737151, compound

HRID 2051101Notes

Reaction equation

HRID 2051101 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([CH3:22])[N:17]([CH3:23])[C:16]2=[O:24])=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].S(=O)(=O)(O)O>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([CH3:22])[N:17]([CH3:23])[C:16]2=[O:24])=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 19832675HCID 19832675, compound

Product 1

HCID 19737151HCID 19737151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 35 g of isopropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate, 165 ml of concentrated sulphuric acid and 165 ml of methylene chloride is stirred well at room temperature for 30 minutes. Subsequently, the reaction mixture is poured cautiously onto 500 g of ice. The aqueous mixture is extracted twice with 250 ml of ethyl acetate each time and the organic phase is extracted three times with 200 ml of saturated sodium bicarbonate solution each time. The aqueous sodium bicarbonate solutions are combined and acidified with concentrated sulphuric acid. The separated product is extracted twice with 600 ml of ethyl acetate each time and the organic phases are washed twice with 200 ml of water each time, dried over anhydrous magnesium sulphate and concentrated. In this manner there is obtained 2-chloro-5-[3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidinyl]-4-fluorobenzoic acid which can be purified further by digestion in ethanol. M.p. 236°-239° C.

Workup

  1. extractionThe aqueous mixture is extracted twice with 250 ml of ethyl acetate each time
  2. extractionthe organic phase is extracted three times with 200 ml of saturated sodium bicarbonate solution each time
  3. extractionThe separated product is extracted twice with 600 ml of ethyl acetate each time
  4. washthe organic phases are washed twice with 200 ml of water each time
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-48f20cc34f4b470b8ee5ef6be74ab9c7
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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