Guanidine Hydrochloride → HCID 18945440, compound

HRID 399870Notes

Reaction equation

HRID 399870 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[C:10]([C:12]1[CH:13]=[C:14]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:15]=[C:16]([CH:20]=1)[C:17]([OH:19])=O)#[N:11].Cl.[NH2:27][C:28]([NH2:30])=[NH:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:10]([C:12]1[CH:13]=[C:14]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:15]=[C:16]([CH:20]=1)[C:17]([N:27]=[C:28]([NH2:30])[NH2:29])=[O:19])#[N:11]

Participants

10

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 1670692-Chloro-1-methylpyridinium iodideHCID 18945142HCID 18945142, compound

Product 1

HCID 18945440HCID 18945440, compoundYield 62.4%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (3.6 g) was added to a mixture of 5-cyano-3-(pyrrol-1-yl)benzoic acid (2.0 g), guanidine hydrochloride (2.7 g) and triethylamine (7.2 ml) in N,N-dimethylformamide (30 ml), and the mixture was stirred for 4 hours at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate, tetrahydrofuran and water, and adjusted to pH 10 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with ether to give 2-[5-cyano-3-(pyrrol-1-yl)benzoyl]guanidine (1.49 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed by concentration
  4. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-156620907c0947a4aac9e70f4121b764
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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