2-Chloro-6-methylaniline → HCID 178424119, compound

HRID 1388503Notes

Reaction equation

HRID 1388503 reaction equation
O(CC(C)C)[C:2]([S-:4])=[S:3].[K+].Cl[C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=1[NH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][C:14]1[C:12]2[N:13]=[C:2]([SH:4])[S:3][C:11]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 11430Potassium CarbonateHCID 23675782Potassium isobutylxanthate

Product 1

HCID 178424119HCID 178424119, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 250 g of potassium isobutyl xanthate (about 90% pure) in 400 ml of dimethylformamide is added dropwise to a mixture of 141.5 g of 2-chloro-6-methylaniline and 276 g of potassium carbonate in 1 liter of dimethylformamide at 150° C. in the course of one hour, under a nitrogen atmosphere. The reaction mixture is stirred for about a further 26 hours, whilst cooling intensively. The batch is cooled, freed from salt and then concentrated to dryness. The residue is taken up in 400 ml of water and the mixture is acidified. The 4-methyl-2-mercaptobenzothiazole which precipitates is filtered off, washed with water and dried. 172 g (95% of theory) of 4-methyl-2-mercaptobenzothiazole of melting point 188°-190° C. are obtained.

Workup

  1. temperaturewhilst cooling intensively
  2. temperatureThe batch is cooled
  3. concentrationconcentrated to dryness
  4. customThe 4-methyl-2-mercaptobenzothiazole which precipitates
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9b06297c1bab419290378df2fad8c280
Source dataset
uspto-grants-1984_02
Patent number
US04431813

Reaction notes

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