Sodium hydride → HCID 23276671, compound

HRID 477727Notes

Reaction equation

HRID 477727 reaction equation
[H-].[Na+].C([NH:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([CH3:14])[C:8]=1[Cl:15])(=O)C.[CH3:16][C:17]1[N:21]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:20]=[C:19]([S:28](Cl)(=[O:30])=[O:29])[N:18]=1>O1CCCC1>[Cl:15][C:8]1[C:9]([CH3:14])=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=1[NH:6][S:28]([C:19]1[N:18]=[C:17]([CH3:16])[N:21]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:20]=1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87254Acetamide, N-(2,6-dichloro-3-methylphenyl)-HCID 19872283HCID 19872283, compound

Product 1

HCID 23276671HCID 23276671, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of sodium hydride (8.7 g) in dry tetrahydrofuran (400 ml) was stirred at 25° C., and N-acetyl-2,6-dichloro-3-methylaniline (50.4 g) was added portionwise. After stirring for 15 minutes, 5-methyl-1-(2-pyrimidinyl)-1,2,4-triazole-3-sulphonyl chloride (30 g), prepared by a method analogous to that of Example A was added over 5 minutes. The mixture was stirred at 25° C. for 18 hours and the solvent was removed in vacuo. The residue was treated with 1M sodium hydroxide solution (500 ml) for 5 minutes with stirring, and was then extracted with ethyl acetate (500 ml). The ethyl acetate layer was re-extracted with 1M sodium hydroxide solution (300 ml). The combined aqueous phases were acidified with concentrated hydrochloric acid and the solid was filtered off. Recrystallisation from acetonitrile gave 38 g of the desired product, mp 214°-216° C.

Workup

  1. stirringAfter stirring for 15 minutes
  2. additionwas added over 5 minutes
  3. stirringThe mixture was stirred at 25° C. for 18 hours
  4. customthe solvent was removed in vacuo
  5. additionThe residue was treated with 1M sodium hydroxide solution (500 ml) for 5 minutes
  6. stirringwith stirring
  7. extractionwas then extracted with ethyl acetate (500 ml)
  8. extractionThe ethyl acetate layer was re-extracted with 1M sodium hydroxide solution (300 ml)
  9. filtrationthe solid was filtered off
  10. customRecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-53ae417c98cd4a4ba3f7234a44dd4477
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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