Isoniazid → HCID 178527959, compound

HRID 334510

Reaction equation

HRID 334510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[S:10].[C:11]([NH:19][NH2:20])(=O)[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:19][N:20]=[C:9]1[SH:10]

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 1231711-Chloro-2-isothiocyanatobenzene

Product 1

HCID 178527959HCID 178527959, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-chloro-2-isothiocyanatobenzene 1 (3 g, 17.68 mmol) and isonicotinohydrazide 2 (2.43 g, 17.68 mmol) in acetonitrile was stirred at ambient temperature for 18 hours, concentrated to dryness, and 100 mL of 10% K2CO3 (aq.) was added. The resulting mixture was stirred under reflux for 6 hours. The clear solution was cooled to ambient temperature, washed with ether and acidified with 1N HCl. The solid was collected, washed with H2O and ether, and dried to afford compound 4 (4.3 g). Yield: 86%.

Workup

  1. concentrationconcentrated to dryness, and 100 mL of 10% K2CO3 (aq.)
  2. additionwas added
  3. stirringThe resulting mixture was stirred
  4. temperatureunder reflux for 6 hours
  5. temperatureThe clear solution was cooled to ambient temperature
  6. washwashed with ether
  7. customThe solid was collected
  8. washwashed with H2O and ether
  9. customdried

Sources & evidence

ORD record
ord-7bfce2b59fb747549e83b6259c61ed31
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Linked notes

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