Water → 4-sec-BUTYLTHIO-5,7-DINITRO-2-TRIFLUOROMETHYLBENZIMIDAZOLE

HRID 1974348Notes

Reaction equation

HRID 1974348 reaction equation
[Na].[CH3:2][CH:3]([SH:6])[CH2:4][CH3:5].Cl[C:8]1[C:16]2[NH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[N:13][C:12]=2[C:11]([N+:21]([O-:23])=[O:22])=[CH:10][C:9]=1[N+:24]([O-:26])=[O:25].O>C(O)C>[CH:3]([S:6][C:8]1[C:16]2[NH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[N:13][C:12]=2[C:11]([N+:21]([O-:23])=[O:22])=[CH:10][C:9]=1[N+:24]([O-:26])=[O:25])([CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 105602-ButanethiolHCID 5360545SodiumHCID 1356775774-Chloro-5,7-dinitro-2-trifluoromethylbenzimidazole

Product 1

HCID 214893794-sec-BUTYLTHIO-5,7-DINITRO-2-TRIFLUOROMETHYLBENZIMIDAZOLE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 milliliters of ethanol, 1 gram of sodium (0.04 mole) was reacted with 3.6 grams of 2-butanethiol (0.04 mole). The mixture was stirred for one-half hour. Then 4-chloro-5,7-dinitro-2-trifluoromethylbenzimidazole (6.2 grams; 0.02 mole) was added, and the resulting reaction mixture was stirred overnight, poured into water, acidified, and filtered to separate the desired 4-sec-butylthio-5,7-dinitro-2-trifluoromethylbenzimidazole. It was recrystallized twice from a mixture of benzene and an aliphatic hydrocarbon fraction boiling at 60°-80° C., m.p., 111°-15° C.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred overnight
  3. filtrationfiltered
  4. customto separate the desired 4-sec-butylthio-5,7-dinitro-2-trifluoromethylbenzimidazole
  5. customIt was recrystallized twice from a mixture of benzene
  6. customan aliphatic hydrocarbon fraction boiling at 60°-80° C., m.p., 111°-15° C.

Sources & evidence

ORD record
ord-749beacdde534ab0b2bbb21b806a9724
Source dataset
uspto-grants-1976_12
Patent number
US04000295

Reaction notes

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