HCID 53945002, compound → HCID 178505338, compound

HRID 1981450Notes

Reaction equation

HRID 1981450 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].[CH3:15][S:16]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][C:21]=1[N+:29]([O-:31])=[O:30])(=[O:18])=[O:17]>N1C=CC=CC=1>[CH3:15][S:16]([OH:19])(=[O:18])=[O:17].[CH3:15][S:16]([OH:19])(=[O:18])=[O:17].[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH2:28])=[CH:22][C:21]=2[N+:29]([O-:31])=[O:30])=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

4

Reactant 2

HCID 53945002HCID 53945002, compoundHCID 178479379HCID 178479379, compound

Product 1

HCID 178505338HCID 178505338, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 300 ml of dried pyridine, were dissolved 7.0 g of 4-guanidinobenzoyl chloride hydrochloride and 7.4 g of 4-amidino-2-nitrophenol methanesulfonate. The solution was stirred overnight at room temperature. The precipitate which was formed was collected by filtration, suspended in methanol and filtered. The filtrate and 300 ml of ethyl ether were stirred to precipitate a colorless solid substance which was collected by filtration, dissolved in a small volume of methanol, and stirred together with a saturated sodium bicarbonate solution to precipitate the intended carbonate. The precipitated carbonate was collected by filtration, then air-dried, suspended in a small volume of methanol, admixed with methanesulfonic acid at room temperature. After 10 minutes, ethyl ether was added to the reaction mixture to precipitate crystals. The crystals were collected by filtration, washed thoroughly with ethyl ether to obtain 4-amidino-2-nitrophenyl 4-guanidinobenzoate dimethanesulfonate.

Workup

  1. customThe precipitate which was formed
  2. filtrationwas collected by filtration
  3. filtrationfiltered
  4. stirringThe filtrate and 300 ml of ethyl ether were stirred
  5. customto precipitate a colorless solid substance which
  6. filtrationwas collected by filtration
  7. dissolutiondissolved in a small volume of methanol
  8. stirringstirred together with a saturated sodium bicarbonate solution
  9. customto precipitate the intended carbonate
  10. filtrationThe precipitated carbonate was collected by filtration
  11. customair-dried
  12. customadmixed with methanesulfonic acid at room temperature
  13. waitAfter 10 minutes
  14. additionethyl ether was added to the reaction mixture
  15. customto precipitate crystals
  16. filtrationThe crystals were collected by filtration
  17. washwashed thoroughly with ethyl ether

Sources & evidence

ORD record
ord-c2a8120a495847a68fc976830c4ebba8
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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