4-Chlorophenyl isothiocyanate → HCID 178446858, compound

HRID 1287396Notes

Reaction equation

HRID 1287396 reaction equation
[Na].Cl.[C:3]([NH2:9])(=[NH:8])[CH2:4][CH2:5][CH2:6][CH3:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[S:19])=[CH:13][CH:12]=1>CC(C)=O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:8][C:3](=[NH:9])[CH2:4][CH2:5][CH2:6][CH3:7])=[S:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 164804-Chlorophenyl isothiocyanateHCID 5360545SodiumHCID 11615174Pentanimidamide Hydrochloride

Product 1

HCID 178446858HCID 178446858, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred mixture, prepared by reacting 4.6 g. sodium with 300 ml. dry acetone at room temperature was cooled to 5°C. and 27.3 g. valeramidine hydrochloride was added in one portion. After 20 minutes there was added dropwise during thirty minutes, a solution of 33.8 g. 4-chlorophenyl isothiocyanate in 200 ml. dry acetone while the temperature was maintained at 5° to 10°C. The mixture was stirred for 18 hours at room temperature, filtered and the filtrate was evaporated to dryness under reduced pressure. A solution of the residue in 300 ml. ether was chilled and treated with ethereal hydrogen chloride until acidic and the resulting solid was filtered to give, after recrystallization from acetonitrile 51.1 g. 1-(4-chlorophenyl)-3-(pentanimidoyl)-2-thiourea hydrochloride; m.p. 164°-166°C.

Workup

  1. customA stirred mixture, prepared
  2. additionAfter 20 minutes there was added dropwise during thirty minutes
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. temperatureether was chilled
  6. additiontreated with ethereal hydrogen chloride until acidic and the resulting solid
  7. filtrationwas filtered
  8. customto give
  9. customafter recrystallization from acetonitrile 51.1 g

Sources & evidence

ORD record
ord-851665bfff424eba81bdcc78555369ae
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

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