Dimethylformamide → 2-(Ethylthio)-1-methyl-4-nitro-1H-imidazole

HRID 653080Notes

Reaction equation

HRID 653080 reaction equation
[CH2:1]([SH:3])[CH3:2].CN(C)C=O.[OH-].[K+].[CH3:11][N:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[C:13]1S(C)(=O)=O>O>[CH3:11][N:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[C:13]1[S:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 14797Potassium Hydroxide2×HCID 3316921-methyl-2-methylsulfonyl-4-nitroimidazole

Product 1

HCID 139122322-(Ethylthio)-1-methyl-4-nitro-1H-imidazoleYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl mercaptan (5.14 g, 0.083 mole) was added to dimethylformamide (140 ml) containing potassium hydroxide (4.6 g, 0.08 mole). This was stirred for 90 minutes until all the potassium hydroxide had dissolved. To this solution was added 1-methyl-2-methylsulfonyl-4-nitroimidazole (8.5 g, 0.04 mole) and the reaction stirred for 2 hours at room temperature. The reaction mixture was then added to water (500 ml) and stirred in an ice bath for an additional hour. The crystalline product was filtered off and dried to give 5.6 g of crude product. This was recrystallized from ethanol/water to give 4.3 g of product.

Workup

  1. dissolutionhad dissolved
  2. stirringstirred in an ice bath for an additional hour
  3. filtrationThe crystalline product was filtered off
  4. customdried
  5. customto give 5.6 g of crude product
  6. customThis was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-98dcc45122344eb9aa390776ddb84b53
Source dataset
uspto-grants-1987_06
Patent number
US04675337

Reaction notes

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