Hydrochloric Acid → HCID 178482827, compound

HRID 2351018Notes

Reaction equation

HRID 2351018 reaction equation
[OH:1][CH:2]([C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][N:17](C)[C:18](=O)C(Cl)(Cl)Cl)=[CH:14][CH:15]=1.Cl>C(O)C.[OH-].[Na+]>[OH:1][CH:2]([C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1)[CH2:3][NH:4][C:5]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][NH:17][CH3:18])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178482828HCID 178482828, compound

Product 1

HCID 178482827HCID 178482827, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

9.4 g of N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-[N-methyl-N(trichloroacetyl)aminomethyl]-2-furyl]methylthio]ethyl]guanidine was dissolved in a mixture of 8 ml of ethanol and 47 ml of a 1N aqueous sodium hydroxide solution in a nitrogen atmosphere. The mixture was stirred at room temperature for 2 hours. Then, the mixture was adjusted to pH 9.7 with 6N hydrochloric acid with ice-cooling, a seed crystal was added thereto and the mixture was stirred for 4 hours at room temperature. The crystals deposited were collected by filtration to obtain 6.0 g (yield: 84%) of N-[2-hydroxy-2-(4hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-(methylamino)methyl-2-furyl]methylthio]ethyl]guanidine.

Workup

  1. temperaturecooling
  2. additiona seed crystal was added
  3. stirringthe mixture was stirred for 4 hours at room temperature
  4. filtrationThe crystals deposited were collected by filtration

Sources & evidence

ORD record
ord-b8716ba1b616424897fd69999cf2c3ca
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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