Ammonia → 3-Chloro-4-methoxybenzene-1-carboximidamide--hydrogen chloride (1/1)

HRID 1722005Notes

Reaction equation

HRID 1722005 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6](=[NH:9])OC.[NH3:15]>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([NH2:15])=[NH:9]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13621610HCID 13621610, compound

Product 1

HCID 136216123-Chloro-4-methoxybenzene-1-carboximidamide--hydrogen chloride (1/1)Yield 191.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 3-chloro-4-methoxybenzimidate hydrochloride, (19.9 g, 0.084 mole) was added to a solution of ammonia (12 g) in CH3OH (100 ml) cooled to -78° C. The stirred mixture was allowed to warm to room temperature. After 20 hours, the solution was evaporated to dryness under reduced pressure. The solid residue was triturated with Et2O and collected to yield 17.8 g (96%) of 27, m.p. dec. 243°-245° C. A sample triturated with acetone melted at 241°-243° C. dec.

Workup

  1. temperatureto warm to room temperature
  2. customthe solution was evaporated to dryness under reduced pressure
  3. customThe solid residue was triturated with Et2O
  4. customcollected

Sources & evidence

ORD record
ord-fdbab997700b45428b2316f7faa18ef7
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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