Ammonia → 4-Amino-3-nitrobenzimidamide hydrochloride

HRID 712934Notes

Reaction equation

HRID 712934 reaction equation
[ClH:1].C(O[C:5](=[NH:16])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)C.[NH3:17]>C(O)C>[ClH:1].[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([NH2:16])=[NH:17])=[CH:7][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67073287Ethyl 4-amino-3-nitrobenzimidate hydrochloride

Product 1

HCID 673560924-Amino-3-nitrobenzimidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.5 g, 344 mmol) was suspended in absolute ethanol (750 mL) and then cooled to 0° C. Ammonia was then passed through the solution for a period of 2 h. The flask was tightly sealed and allowed to warm up to room temperature over an 18 h period with stirring. The product was crystallized with diethyl ether and the resulting solid was filtered, washed and dried to give 4-amino-3-nitrobenzamidine monohydrochloride (70.7 g) as an off-white powder.

Workup

  1. customThe flask was tightly sealed
  2. temperatureto warm up to room temperature over an 18 h period
  3. customThe product was crystallized with diethyl ether
  4. filtrationthe resulting solid was filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-37044b772193479bbb4bc4008a68ce34
Source dataset
uspto-grants-2015_11
Patent number
US09181280B2

Reaction notes

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