Guanidine → HCID 19360541, compound

HRID 376897Notes

Reaction equation

HRID 376897 reaction equation
C1N=[CH:4][N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])C=1.[Cl:13][C:14]1[CH:15]=C([CH:20]=[CH:21][C:22]=1[Cl:23])CCN.[NH2:24]C(N)=N>C1COCC1>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:10]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:9][N:8]([C:6]([NH:3][CH3:4])=[O:7])[C:12]([NH2:11])=[NH:24]

Participants

5

Reactant 3

HCID 3520GuanidineHCID 682631,1'-CarbonyldiimidazoleHCID 2179583,4-Dichlorophenethylamine

Product 1

HCID 19360541HCID 19360541, compoundYield 154.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g of CDI were added to a solution of 3.0 g of 3,4-dichlorobenzylmethylamine in 110 ml of THF and it was stirred at RT overnight. After addition of 4.6 g of guanidine, the reaction mixture was again stirred overnight and concentrated on a rotary evaporator, and the residue was stirred with 120 ml of water. The precipitate which was deposited during this process was filtered off with suction, dried in vacuo and dissolved in 50 ml of ethyl acetate and 7 ml of methanol. After addition of ethereal hydrochloric acid and suction filtration of the precipitated product, 3.8 g of N-(3,4-dichlorobenzyl)-N-methylaminocarbonylguanidinehydrochloride were obtained;

Workup

  1. waitthe reaction mixture was again stirred overnight
  2. concentrationconcentrated on a rotary evaporator
  3. stirringthe residue was stirred with 120 ml of water
  4. filtrationwas filtered off with suction
  5. customdried in vacuo
  6. dissolutiondissolved in 50 ml of ethyl acetate
  7. additionAfter addition of ethereal hydrochloric acid and suction filtration of the precipitated product

Sources & evidence

ORD record
ord-ed9317bb41224560b9c4d2f36921ea2b
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

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