Ammonia → HCID 70565428, compound

HRID 128418Notes

Reaction equation

HRID 128418 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)#[N:3].Cl.C(OC(=[NH:37])C1C=CC(C=CC2C=CC=CC=2)=CC=1)C.C(=N)([O-])C1C=CC=CC=1.N>CO.C(O)C.C1C=CC=CC=1>[ClH:1].[CH:10]([C:7]1[CH:8]=[CH:9][C:4]([C:2]([NH2:37])=[NH:3])=[CH:5][CH:6]=1)=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6096084-[(E)-2-Phenylethenyl]benzonitrileHCID 21972543BenzimidateHCID 70566768HCID 70566768, compound

Product 1

HCID 70565428HCID 70565428, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydrogen chloride is bubbled through a mixture of 4-cyanostilbene (13.5 g., 0.065 mole), obtained according to the method of Belgian Pat. No. 641,415 (Chem. Abs. 63: 3092 g (1965)), in 35 ml. of dry benzene and 17.5 ml. of absolute ethanol at 0° to 5° C. for a period of 3 hr. The reaction is maintained at 0° to 5° C. for 48 hr. and the solvent and excess hydrogen chloride removed under reduced pressure. The residue stirred with 50 ml. of dry benzene and collected provides 13.0 g. of ethyl-4-styrylbenzimidate hydrochloride. A methanol solution of the benzimidate salt is cooled to 5° to 10° C., saturated with ammonia and heated at a temperature of 100° C. for a period of 3 hr. in an enclosed container. Concentration of the reaction mixture provides 4-styrylbenzamidine hydrochloride.

Workup

  1. customobtained
  2. temperatureThe reaction is maintained at 0° to 5° C. for 48 hr
  3. customand the solvent and excess hydrogen chloride removed under reduced pressure
  4. customof dry benzene and collected
  5. customprovides 13.0 g

Sources & evidence

ORD record
ord-193a6871017a43a3aedb6aa98309eac9
Source dataset
uspto-grants-1981_03
Patent number
US04259482

Reaction notes

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