1-Chloro-2-isothiocyanatobenzene → HCID 178527962, compound

HRID 334513Notes

Reaction equation

HRID 334513 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[S:10].[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=O)[CH:15]=[CH:14][N:13]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[CH:17]=2)=[N:20][N:21]=[C:9]1[SH:10]

Participants

4

Reactant 2

HCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 2362062-Chloropyridine-4-carbohydrazide

Product 1

HCID 178527962HCID 178527962, compoundYield 571%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-chloro-2-isothiocyanatobenzene 1 (0.4 g, 2.33 mmol) and 2-chloropyridine-4-carbohydrazide 11 (0.4 g, 2.33 mmol) in DMF was stirred at ambient temperature for 18 hours, concentrated to dryness, and 20 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 13 (4.3 g). Yield: 86%.

Workup

  1. concentrationconcentrated to dryness, and 20 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-a9f247e8e7a24f389e5e7a56d4ea3ef2
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

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