N,N-Dimethylaniline → HCID 19980554, compound

HRID 1461373Notes

Reaction equation

HRID 1461373 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC1[S:12][C:13]([N+:17]([O-:19])=[O:18])=[C:14]([Cl:16])[N:15]=1.O>C(#N)C>[Cl:16][C:14]1[N:15]=[C:1]([N:2]([CH3:9])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[S:12][C:13]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 962WaterHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 19980554HCID 19980554, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

12.7 g (0.105 mol) of N,N-dimethylaniline are added to a solution of 19.9 g (0.1 mol) of 2,4-dichloro-5-nitrothiazole in 250 ml of acetonitrile and the reaction mixture is stirred under reflux for 75 hours. The solvent is then stripped off in vacuo and the solid residue is stirred into water, filtered off, washed with water and dried. 25.8 g (95.7 % of theory) of 4-chloro-2-(N-methyl-N-phenylamino)-5-nitrothiazole are obtained. The compound can be recrystallized from cyclohexane and can be sublimed at about 110° C. to 120° C./0.1 mbar. Melting point 136° C. to 137° C.

Workup

  1. temperatureunder reflux for 75 hours
  2. filtrationfiltered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4989e7878c4148a78835a488917f2c96
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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