Thionyl Chloride → HCID 54489017, compound

HRID 258233Notes

Reaction equation

HRID 258233 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:15]([CH3:21])[C:14]2=[O:22])=[CH:8][C:4]=1[C:5](O)=[O:6])#[N:2].S(Cl)([Cl:25])=O>CN(C)C=O>[C:1]([C:3]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:15]([CH3:21])[C:14]2=[O:22])=[CH:8][C:4]=1[C:5]([Cl:25])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19737156HCID 19737156, compound

Product 1

HCID 54489017HCID 54489017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 3.0 g of finely pulverised 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid, 30 ml of freshly distilled thionyl chloride and 3 drops of dimethylformamide is heated at reflux temperature for 1 hour with stirring, after which a clear solution has formed. The mixture is then concentrated to dryness by evaporation to yield 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid chloride, m.p. 160° C., which is used, unpurified, as the starting material in the next reaction step.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. customafter which a clear solution has formed
  4. concentrationThe mixture is then concentrated to dryness by evaporation

Sources & evidence

ORD record
ord-b00c40f099204a37a9e60f9cdc608a34
Source dataset
uspto-grants-1993_11
Patent number
US05266554

Reaction notes

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