M-Phenylenediamine → HCID 21434863, compound

HRID 2398194Notes

Reaction equation

HRID 2398194 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([NH2:18])[CH:12]=2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 21434863HCID 21434863, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of p-chlorophenyl isothiocyanate (39.6 g.) in chloroform (100 ml.) is added dropwise with stirring to a solution of m-phenylene diamine (25.2 g.) in chloroform (200 ml.) at room temperature. The mixture is stirred for 1 hour after the addition is complete, and the precipitated solid is filtered off, washed with chloroform and dried to give 1-(p-chlorophenyl)-3-(m-aminophenyl)thiourea, m.p. 132°-133.5° C. This product (20 g.) is dissolved in ethanol saturated with ammonia gas (300 ml.), yellow mercuric oxide (17.2 g.) is added and the mixture is stirred for 24 hours at room temperature. The black precipitate is filtered off and washed thoroughly with boiling ethanol, and the filtrate is evaporated to dryness. The residue is dissolved in chloroform, the solution is filtered and an excess of ethereal hydrochloric acid is added to the filtrate, followed by a large volume of ether. The oily precipitate is allowed to solidify, is triturated with fresh dry ether, and is filtered off and dried, to give 1-(p-chlorophenyl)-3-(m-aminophenyl)guanidine dihydrochloride, m.p. 236°-238° C.

Workup

  1. additionafter the addition
  2. filtrationthe precipitated solid is filtered off
  3. washwashed with chloroform
  4. customdried

Sources & evidence

ORD record
ord-d756d3d0be0a402bb0f2efa49c8a9f76
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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