4-Chlorophenyl isothiocyanate → HCID 131717393, compound

HRID 1196765Notes

Reaction equation

HRID 1196765 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[CH:3][C:4]([O:6]CC)=O.[H-].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:15])[NH:1][C:26]2=[S:27])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 164804-Chlorophenyl isothiocyanateHCID 24758Sodium hydrideHCID 67836558HCID 67836558, compound

Product 1

HCID 131717393HCID 131717393, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.3 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a solution of 0.5 g of sodium hydride (purity: 55%) in 20 ml of dimethylformamide with stirring at 0° C. The mixed solution was stirred at room temperature for 15 minutes, then cooled to 0° C. and added with 1.7 g of 4-chlorophenyl isothiocyanate. The resulting solution was heated to room temperature and further stirred at 100° C. for one hour. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding 100 ml of water. This aqueous solution was washed twice with diethyl ether and added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid. The aqueous mixture was extracted with 100 ml of ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away to obtain 2.1 g of a crude product. This crude product was washed with heated diisopropyl ether and dried to obtain 1.0 g of the objective compound.

Workup

  1. stirringThe mixed solution was stirred at room temperature for 15 minutes
  2. temperaturecooled to 0° C.
  3. temperatureThe resulting solution was heated to room temperature
  4. stirringfurther stirred at 100° C. for one hour
  5. distillationThen the solvent was distilled away under reduced pressure
  6. dissolutionthe residue was dissolved
  7. additionby adding 100 ml of water
  8. washThis aqueous solution was washed twice with diethyl ether
  9. additionadded to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid
  10. extractionThe aqueous mixture was extracted with 100 ml of ethyl acetate
  11. washwashed with water
  12. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  13. distillationThen the solvent was distilled away
  14. customto obtain 2.1 g of a crude product
  15. washThis crude product was washed with heated diisopropyl ether
  16. customdried

Sources & evidence

ORD record
ord-5ba296ac2459467d8f7bec15818ad24e
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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