Guanidine Hydrochloride → HCID 59395105, compound

HRID 657705Notes

Reaction equation

HRID 657705 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]([NH2:7])=[NH:6].[CH:8]1[C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][C:9]=1[C:21](OC)=[O:22]>CN(C=O)C>[NH2:6][C:5]([NH2:7])=[N:4][C:21]([C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:19][C:20]=2[CH:8]=1)=[O:22]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 24758Sodium hydrideHCID 11299083Methyl 9H-carbazole-2-carboxylate

Product 1

HCID 59395105HCID 59395105, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 192 mg portion of sodium hydride (60%) was added to 6.5 ml DMF solution of 573 mg guanidine hydrochloride and stirred at room temperature for 1 hour. A 6.5 ml DMF solution of 270 mg methyl 9H-carbazole-2-carboxylate was added to this solution, followed by stirring at 70° C. for 2.5 hours. After spontaneous cooling to room temperature and subsequent evaporation of the solvent, water was added thereto and the thus precipitated solid was purified by Chromatorex (methanol/chloroform) to obtain 236 mg of N-(diaminomethylene)-9H-carbazole-2-carboxamide as a pale yellow solid.

Workup

  1. stirringby stirring at 70° C. for 2.5 hours
  2. temperatureAfter spontaneous cooling to room temperature
  3. customsubsequent evaporation of the solvent, water
  4. additionwas added
  5. customthe thus precipitated solid was purified by Chromatorex (methanol/chloroform)

Sources & evidence

ORD record
ord-aef89b226bd14131955e9038e65977ce
Source dataset
uspto-grants-2011_12
Patent number
US08076348B2

Reaction notes

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