Ammonia → 1-(3-Isopropylguanidino)-3-(3-p-chlorophenylureido)benzene hydrochloride

HRID 2398195Notes

Reaction equation

HRID 2398195 reaction equation
[CH:1]([NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[O:15])[CH:8]=1)([CH3:3])[CH3:2].[NH3:25]>C(O)C>[ClH:23].[CH:1]([NH:4][C:5](=[NH:25])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[O:15])[CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 538688891-(3-Isopropylthioureido)-3-(3-p-chlorophenylureido)benzene

Product 1

HCID 1784575781-(3-Isopropylguanidino)-3-(3-p-chlorophenylureido)benzene hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Isopropylthioureido)-3-(3-p-chlorophenylureido)-benzene (1.5 crystallized g.) is dissolved in ethanol (100 ml.) saturated with ammonia gas, and the solution stirred for 24 hours at room temperature with yellow mercuric oxide (1.02 g.). The mixture is boiled for 1/2 hour to coagulate the fine precipitate, and is filtered hot. The solid is washed thoroughly with 3 × 50 ml. portions of boiling ethanol, and the filtrate and washings are combined and evaporated to dryness. The remaining gum is dissolved in methanol (10 ml.) and saturated ethereal hydrogen chloride (3 ml.) is added followed by dry ether (150 ml.). The precipitated oil rapidly solidifies, is filtered off and crystallised from ethanol to give 1-(3-isopropylguanidino)-3-(3-p-chlorophenylureido)benzene hydrochloride, m.p. 224°-225° C.

Workup

  1. filtrationis filtered hot
  2. washThe solid is washed thoroughly with 3 × 50 ml
  3. customevaporated to dryness
  4. dissolutionThe remaining gum is dissolved in methanol (10 ml.)
  5. additionsaturated ethereal hydrogen chloride (3 ml.) is added
  6. filtrationis filtered off
  7. customcrystallised from ethanol

Sources & evidence

ORD record
ord-1dd93b45f36845bbbeb3b8dae3e43e40
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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