M-Phenylenediamine → HCID 21434867, compound

HRID 2398199Notes

Reaction equation

HRID 2398199 reaction equation
[CH2:1]([N:5]=[C:6]=[S:7])[CH:2]([CH3:4])[CH3:3].[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1>C(Cl)Cl>[CH2:1]([NH:5][C:6]([NH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([NH2:15])[CH:9]=1)=[S:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 68960Isobutyl isothiocyanate

Product 1

HCID 21434867HCID 21434867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyl isothiocyanate (16 g.) is added dropwise with stirring to a solution of m-phenylenediamine (17 g.) in methylene chloride (500 ml.) at room temperature. After 16 hours the solution is concentrated until crystallization begins. The mixture is diluted with benzene, and the product is filtered off, washed with benzene and dried. The 1-isobutyl-3-m-aminophenylthiourea thus obtained (23 g.) is dissolved in ethanol (250 ml.) saturated with ammonia gas, and stirred for 48 hours at room temperature with yellow mercuric oxide (28.2 g.). The mixture is filtered, the solids washed thoroughly with boiling ethanol and the combined filtrate and washings are evaporated to dryness. The residue is dissolved in a little methanol, treated with excess saturated ethereal hydrogen chloride and a large volume of dry ether. A red oil separates, which is triturated with fresh ether until solid, and the solid is filtered off and crystallized from methanol/ethyl acetate, to give 1-isobutyl-3-m-aminophenylguanidine dihydrochloride, m.p. 215° C.

Workup

  1. concentrationAfter 16 hours the solution is concentrated until crystallization
  2. additionThe mixture is diluted with benzene
  3. filtrationthe product is filtered off
  4. washwashed with benzene
  5. customdried

Sources & evidence

ORD record
ord-de4065547441496da9238ac696b35a00
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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