Hydrochloric Acid → 1-Isothiocyanato-4-[(3-phenylpropyl)thio]benzene

HRID 1415347Notes

Reaction equation

HRID 1415347 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:19]([SH:21])#N.N>ClC1C=CC=CC=1Cl>[C:1]1([CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:12]=[CH:13][C:14]([N:15]=[C:19]=[S:21])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13417437AmthioHCID 214818444-(3'-Phenyl-propylthio)-aniline

Product 1

HCID 214818391-Isothiocyanato-4-[(3-phenylpropyl)thio]benzene

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

6.4 g of the 4-(3'-phenyl-propylthio)-aniline obtained under (b) is dissolved in 50 ml of 1,2-dichlorobenzene, and the solution is saturated at room temperature, with stirring, with anhydrous hydrogen chloride. There is subsequently added 2.5 g of ammonium rhodanide, and the whole is heated, with the continuous introduction of hydrogen chloride, for 6 hours at 130° to 140°. The undissolved constituents are filtered off, and the filtrate is chromatographed through silica gel with 1,2-dichlorobenzene as the eluant. There is obtained pure 4-(3'-phenyl-propylthio)-phenyl-isothiocyanate having a refractive index of nD25 = 1.6672 (= Compound No. 1).

Workup

  1. customis saturated at room temperature
  2. filtrationThe undissolved constituents are filtered off
  3. customthe filtrate is chromatographed through silica gel with 1,2-dichlorobenzene as the eluant

Sources & evidence

ORD record
ord-52d6541a16194b4d8a2183c55ec5afe6
Source dataset
uspto-grants-1977_01
Patent number
US04004907

Reaction notes

Loading…