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Hydrochloric Acid → Ethyl 2-cyanobenzimidate hydrochloride

HRID 397500
Notes
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Reaction equation

HRID 397500 reaction equation
[C:1](#[N:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]#[N:5].[ClH:11].[CH2:12]([OH:14])[CH3:13]>C(Cl)(Cl)Cl>[ClH:11].[CH2:12]([O:14][C:1](=[NH:10])[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7042Phthalonitrile

Product 1

HCID 69589883Ethyl 2-cyanobenzimidate hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of phthalonitrile (70 g, 0.55 mol) in ethanol (100 ml) and chloroform (200 ml) was warmed and then cooled to 0° C. The reaction mixture was saturated with HCl (g) and then aged at 0° C. for 2 weeks. The resultant precipitate was filtered and washed with chloroform. Dilution of the filtrate with ether produced additional 2-cyano-benzimidic acid ethyl ester hydrochloride.

Workup

  1. temperaturewas warmed
  2. waitaged at 0° C. for 2 weeks
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with chloroform

Sources & evidence

ORD record
ord-10161b5476884fc787cf18998afc649d
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610701B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes