Phosphorus oxychloride → 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid chloride

HRID 576797Notes

Reaction equation

HRID 576797 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[C:12]([S:34]([OH:37])(=O)=[O:35])[CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].P(Cl)(Cl)([Cl:40])=O>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[C:12]([S:34]([Cl:40])(=[O:37])=[O:35])[CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 715138621-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid

Product 1

HCID 867239071-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of the compound prepared in Example 191 (10.0 g) in acetonitrile (70 ml) was added phosphorus oxychloride (7.04 ml) and the resulting mixture was stirred at 90° C. for two hours. The mixture was concentrated on evaporator instrument under reduced pressure and to the residue were then added ethyl acetate (50 ml) and hexane (50 ml) and the mixture was stirred for thirty minutes. The precipitated solids were collected by filtration and washed with ethyl acetate/hexane=1/1 to afford 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonylchloride (10.3 g). UPLC/MS 550 (M+H)/1.08 min. (measurement condition 9).

Workup

  1. concentrationThe mixture was concentrated on evaporator instrument under reduced pressure and to the residue
  2. stirringadded ethyl acetate (50 ml) and hexane (50 ml) and the mixture was stirred for thirty minutes
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with ethyl acetate/hexane=1/1

Sources & evidence

ORD record
ord-e9e9a4934c134b92b4af53e51732cd8d
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

Loading…