Hydrochloric Acid → HCID 57288043, compound

HRID 654800Notes

Reaction equation

HRID 654800 reaction equation
C([NH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[S:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[CH:13][C:12]([C:24]#[N:25])=[N:11]2)=[CH:6][CH:5]=1)=O.[H-].[Na+].I[CH3:29].Cl.CN(C)[CH:33]=[O:34]>>[CH:33]([CH2:29][NH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[S:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[CH:13][C:12]([C:24]#[N:25])=[N:11]2)=[CH:6][CH:5]=1)=[O:34]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19886107HCID 19886107, compound

Product 1

HCID 57288043HCID 57288043, compound

Conditions

Temperature
0 °C

Procedure

A solution of 1-[4-(formylamino)phenyl]-5-[5-(methylsulfonyl)-2-thienyl]pyrazole-3-carbonitrile (1.1 g) in N,N-dimethylformamide (3 ml) was added dropwise to a suspension of sodium hydride (60%; 118 mg) in N,N-dimethylformamide (2 ml). The mixture was stirred at 0° C. for 30 minutes. To the mixture was added dropwise a solution of iodomethane (0.84 g) in N,N-dimethylformamide (2 ml) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour, poured into an ice-cooled dilute hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ethanol to give crystals of 1-[4-(N-formylmethylamino)phenyl]-5-[5-(methylsulfonyl)-2-thienyl]pyrazole -3-carbonitrile (1 g).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f51f3ef91ec34e72b29fb3c507388adf
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

Loading…