HCID 22155118, compound → HCID 22155112, compound

HRID 1110343Notes

Reaction equation

HRID 1110343 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([S:11][CH3:12])[C:8]([S:13][CH3:14])=[CH:7][C:6]=1[S:15]C)(=O)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH3:2][C:1]1[S:15][C:6]2[CH:7]=[C:8]([S:13][CH3:14])[C:9]([S:11][CH3:12])=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 1

HCID 22155118HCID 22155118, compound

Product 1

HCID 22155112HCID 22155112, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2-Methyl-5,6-dimethylthiobenzothiazole was prepared by combining N-acetyl-2,4,5-trimethylthioaniline (20 g , 0.073 mol) and phosphoryl chloride (40 mL) and heating the mixture on a steam bath for 10 min. During this time the reaction mixture solidified. The solid was collected, washed with ether and dried, affording 27 g of the hydrochloride salt. The free base was prepared by dissolving the salt in a mixture of 300 mL of ether and 300 mL of methanol and adding 35 mL of triethylamine. The solvents were evaporated, the solid was collected, slurried with distilled water, collected, and washed with warm water and dried (16 g, 91% yield), mp 79-81° C.

Workup

  1. temperatureheating the mixture on a steam bath for 10 min
  2. customThe solid was collected
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-0014f3099fba47329152279772ff2fd7
Source dataset
uspto-grants-1990_12
Patent number
US04975362

Reaction notes

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