Guanidine → HCID 86755113, compound

HRID 376900Notes

Reaction equation

HRID 376900 reaction equation
CNCC1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:5]=1.C1[N:25]=[CH:24][N:23]([C:26]([N:28]2C=N[CH:30]=[CH:29]2)=[O:27])[CH:22]=1.[NH2:33]C(N)=N>C1COCC1>[CH3:20][S:17]([OH:18])(=[O:19])=[O:27].[CH3:22][N:23]([C:26]([NH:28][CH2:29][C:30]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:5]=1)=[O:27])[C:24]([NH2:25])=[NH:33]

Participants

5

Reactant 3

HCID 3520GuanidineHCID 682631,1'-CarbonyldiimidazoleHCID 19360562HCID 19360562, compound

Product 1

HCID 86755113HCID 86755113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of N-methyl-N-(3-methylsulfonyl-4-phenoxybenzyl)amine and 0.7 g of CDI dissolved in 25 ml of THF were stirred at RT for 2 h. 1.1 g of guanidine were added, the mixture was stirred overnight and the solvent was distilled off on a rotary evaporator. The residue was taken up in 100 ml of water, adjusted to pH 7.6 with 10 percent hydrochloric acid and extracted twice with ethyl acetate. After concentrating, the guanidine derivative obtained was dissolved again in ethyl acetate, and by adding the equivalent amount of methanesulfonic acid was precipitated as the methanesulfonate. 0.8 g of N-methyl-N-(3-methylsulfonyl-4-phenoxybenzyl)aminocarbonylguanidine methanesulfonate was obtained;

Workup

  1. stirringthe mixture was stirred overnight
  2. distillationthe solvent was distilled off on a rotary evaporator
  3. extractionextracted twice with ethyl acetate
  4. concentrationAfter concentrating

Sources & evidence

ORD record
ord-5be9fcf6ddd84a68a557386885400762
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

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