Carbon Disulfide → 3H-1,2,4-Dithiazole-3-thione, 5-phenyl-

HRID 1039542Notes

Reaction equation

HRID 1039542 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:12](=[S:14])=[S:13]>N1C=CC=CC=1>[C:2]1([C:1]2[S:8][S:14][C:12](=[S:13])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 683563Thiobenzamide

Product 1

HCID 122041713H-1,2,4-Dithiazole-3-thione, 5-phenyl-Yield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of thiobenzamide (100 g, 0.74 mol, Alfa Aesar, Ward Hill, Mass.) was added dropwise to a stirred suspension of NaH (22 g, 0.74 mol, 60% suspension in mineral oil) in pyridine (1 L) at −15° C. followed by the addition of carbon disulfide (122 g, 1.6 mol). The reaction mixture was stirred for 3 h at −10° C. and the solvent was evaporated. The residue was treated with ether, the solution was removed, and the insoluble material was treated in water (1 L). The precipitate was filtered off, and the clear solution was cooled to 0-4° C. and acidified with dilute hydrochloric acid. The crystalline precipitate was collected, washed with water, and dried to yield compound 7 (37.5 g, 24%).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was treated with ether
  3. customthe solution was removed
  4. additionthe insoluble material was treated in water (1 L)
  5. filtrationThe precipitate was filtered off
  6. temperaturethe clear solution was cooled to 0-4° C.
  7. customThe crystalline precipitate was collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-8ed9b0c6e582469a890c14367a649002
Source dataset
uspto-grants-2013_10
Patent number
US08552175B2

Reaction notes

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