Ammonia → HCID 70565428, compound

HRID 66201Notes

Reaction equation

HRID 66201 reaction equation
[ClH:1].C(C1C=CC=CC=1C=CC1C=CC=CC=1)#[N:3].Cl.C(O[C:22](=[NH:37])[C:23]1[CH:28]=[CH:27][C:26]([CH:29]=[CH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)C.C(=N)([O-])C1C=CC=CC=1.N>CO.C(O)C.C1C=CC=CC=1>[ClH:1].[CH:29]([C:26]1[CH:25]=[CH:24][C:23]([C:22]([NH2:37])=[NH:3])=[CH:28][CH:27]=1)=[CH:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21972543BenzimidateHCID 669783742-(2-Phenylethenyl)benzonitrileHCID 70566768Ethyl-4-styrylbenzimidate hydrochloride

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 4L -cyanostilbene (13.5 g., 0.065 mole), obtained according to the method of Belgian Patent 641,415 (Chem. Abs. 63: 3092g (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-ede24159cbec40529c04f2b7b61d477d
Source dataset
uspto-grants-1978_12
Patent number
US04130663

Reaction notes

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