N,N-Dimethylthioformamide → 6-Methyl-5-nitrobenzothiazole

HRID 1936589Notes

Reaction equation

HRID 1936589 reaction equation
Cl[C:2]1[C:3]([N+:12]([O-])=O)=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.CN(C)[CH:17]=[S:18]>>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]2[N:12]=[CH:17][S:18][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 69794N,N-DimethylthioformamideHCID 2538025-Chloro-2,4-dinitrotoluene

Product 1

HCID 224622156-Methyl-5-nitrobenzothiazole

Conditions

Temperature
120 °C

Procedure

A mixture of 1.6 g of 5-chloro-2,4-dinitrotoluene and 20 mL of N,N-dimethyl-thioformamide is heated to 120° C. for 16 hours. After cooling to room temperature, the mixture is purified by flash column chromatography on silica gel, eluting with 3% to 10% ethyl acetate/hexanes to provide 0.78 g of 6-methyl-5-nitrobenzothiazole as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture is purified by flash column chromatography on silica gel
  3. washeluting with 3% to 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-134a7e30664c40f18f61160a6911d1c5
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

Loading…