Hydrochloric Acid → HCID 21433375, compound

HRID 2398635Notes

Reaction equation

HRID 2398635 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7](=[S:13])[S:8][CH2:9][C:10](Cl)=[CH2:11])=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:2]1([CH3:1])[CH:15]=[CH:14][C:5]([N:6]=[C:7]2[S:13][C:10]([CH3:11])=[CH:9][S:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 21433378HCID 21433378, compound

Product 1

HCID 21433375HCID 21433375, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloroallyl 4-methyldithiocarbanilate (7.3 g, 0.0286 mol) and concentrated hydrochloric acid (9.1 ml 0.112 mol) are mixed and heated at reflux temperature for 2 hours. The resulting solution is cooled, diluted with water, and neutralized with sodium carbonate. The reaction mixture is extracted with ether. The ether extract is washed with 6N hydrochloric acid and the aqueous layer is separated, neutralized with sodium carbonate, and extracted with ether. The ether phase is separated, washed with water and dried over anhydrous magnesium sulfate. The ether is evaporated to dryness in vacuo to leave 5.0 g of crude 2-(p-tolyl)imino-4-methyl-1,3-dithiole, a brown oil which crystallizes on standing. The crystalline mass is triturated with petroleum ether, filtered off and dried to yield 2.7 g of purified product melting at from 46.5° C. to 49.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe resulting solution is cooled
  4. extractionThe reaction mixture is extracted with ether
  5. extractionThe ether extract
  6. washis washed with 6N hydrochloric acid
  7. customthe aqueous layer is separated
  8. extractionextracted with ether
  9. customThe ether phase is separated
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe ether is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-b59238bd078d4d0495e9ee9232770f6d
Source dataset
uspto-grants-1977_05
Patent number
US04025532

Reaction notes

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