Guanidine Hydrochloride → HCID 23223387, compound

HRID 399875Notes

Reaction equation

HRID 399875 reaction equation
[F:1][C:2]([F:24])([F:23])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16](OC)=[O:17])[CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:4].Cl.[NH2:26][C:27]([NH2:29])=[NH:28].C[O-].[Na+]>CN(C)C=O>[F:1][C:2]([F:24])([F:23])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([N:26]=[C:27]([NH2:29])[NH2:28])=[O:17])[CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18945297HCID 18945297, compound

Product 1

HCID 23223387HCID 23223387, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-(3-trifluoromethylsulfonylaminophenyl)-benzoate (1.7 g) was added to the mixture of guanidine hydrochloride (2.26 g) and 28% methanolic sodium methoxide (4.1 ml) in N,N-dimethylformamide (17 ml) and the reaction mixture was stirred for 6 hours at ambient temperature. After evaporating the solvent, the residue was poured into the mixture of ethyl acetate (50 ml) and water (50 ml). The mixture was adjusted to pH 6.2 with 10% hydrochloric acid. The crystalline product was collected by filtration, washed successively with water and methanol and dried in vacuo to afford 2-[3-(3-trifluoromethylsulfonylaminophenyl) benzoyl]guanidine (0.28 g).

Workup

  1. customAfter evaporating the solvent
  2. additionthe residue was poured into the mixture of ethyl acetate (50 ml) and water (50 ml)
  3. filtrationThe crystalline product was collected by filtration
  4. washwashed successively with water and methanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-36fbcbc7b5384239afba656d6a99ecfb
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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