Ammonia → HCID 178483157, compound

HRID 1732580Notes

Reaction equation

HRID 1732580 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:17][C:15]=2[CH:16]=1)SC)#[N:2].[NH3:25]>C(O)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:17][C:15]=2[CH:16]=1)=[NH:25])#[N:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20303949HCID 20303949, compound

Product 1

HCID 178483157HCID 178483157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-cyano-N'-[2-(6-dimethylaminomethyl)-2-benzofuranylmethylthio)ethyl]-S-methylisothiourea (Example 1, Step F) (6.27 g., 0.0173 mole) and ammonia (12 g.) in ethanol (65 ml.) is heated in a sealed vessel for 36 hours at 55°-60° C. Volatile materials are then removed by distillation at reduced pressure. The residual oil consisting of the nearly pure product is purified by column chromatography on 85 g. of silica gel with elution by a 10% solution of methanol in chloroform affording N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]guanidine.

Workup

  1. customVolatile materials are then removed by distillation at reduced pressure
  2. customis purified by column chromatography on 85 g
  3. washof silica gel with elution by a 10% solution of methanol in chloroform

Sources & evidence

ORD record
ord-6798216f34b64a229d7992626a07f7d5
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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