Phosphorus oxychloride → HCID 178481247, compound

HRID 32547Notes

Reaction equation

HRID 32547 reaction equation
[NH2:1][C:2]1[C:3]([SH:9])=[N:4][CH:5]=[N:6][C:7]=1[SH:8].[CH3:10][N:11]1[C:15]([C:16](O)=O)=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=[CH:12]1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][N:11]1[C:15]([C:16]2[S:9][C:3]3[N:4]=[CH:5][N:6]=[C:7]([SH:8])[C:2]=3[N:1]=2)=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 179657941-Methyl-4-phenyl-1H-imidazole-5-carboxylic acid2×HCID 1785081365-Aminopyrimidine-4,6-dithiol2×

Product 1

HCID 178481247HCID 178481247, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

5-Aminopyrimidin-4,6-dithiol (Intermediate 41) (1.26 g) and 1-methyl-4-phenyl-1H-imidazole-5-carboxylic acid (Intermediate 3) (1.6 g) were dissolved/ suspended in pyridine (30 mL) and heated at 55° C. under an inert atmosphere. POCl3 (1.55 mL) was added dropwise over 5 minutes, after 2 hours the reaction mixture was concentrated in vacuo and 2M NaOH (15 mL) added cautiously. After stirring for 15 minutes, concentrated HCl was added to acidify to pH 5, the precipitated solid was filtered, washed with water (40 mL), diethyl ether (50 mL) then dried under high vacuum to give the title compound as a yellow solid (1.83 g, 71%);

Workup

  1. concentrationwas concentrated in vacuo and 2M NaOH (15 mL)
  2. additionadded cautiously
  3. additionconcentrated HCl was added
  4. filtrationthe precipitated solid was filtered
  5. washwashed with water (40 mL), diethyl ether (50 mL)
  6. customthen dried under high vacuum

Sources & evidence

ORD record
ord-3fff5a50a5f24975ad5115bf07fc0113
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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