Hydrochloric Acid → HCID 178442801, compound

HRID 1437059Notes

Reaction equation

HRID 1437059 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[ClH:13].Cl.[F:15][C:16]([F:32])([F:31])[C:17]1[CH:30]=[CH:29][C:20]([CH2:21][NH:22][C:23]([NH:25][C:26]([NH2:28])=[NH:27])=[NH:24])=[CH:19][CH:18]=1>C(O)C>[ClH:13].[NH2:28][C:26]1[NH:25][C:23]([NH:22][CH2:21][C:20]2[CH:29]=[CH:30][C:17]([C:16]([F:15])([F:31])[F:32])=[CH:18][CH:19]=2)=[N:24][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[N:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8186UndecanalHCID 178479485HCID 178479485, compound

Product 1

HCID 178442801HCID 178442801, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 ml of ethanol, 5.3 ml (25.7 mmol) of 1-undecanal and 0.7 ml of concentrated hydrochloric acid were added to 5.01 g (16.9 mmol) of N1-(4-trifluoromethylbenzyl)-biguanide hydrochloride, and the mixture was refluxed for 24 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The first main fraction eluted with a mixture of chloroform and methanol (9:1.5) was recrystallized from 80% aqueous acetonitrile to obtain 1.41 g of colorless crystals (1) having a melting point of 163 to 166° C., and the second main eluate was recrystallized from 80% aqueous acetonitrile to obtain 0.87 g of colorless crystals (2) having a melting point of 208 to 211° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography
  4. washThe first main fraction eluted with a mixture of chloroform and methanol (9:1.5)
  5. customwas recrystallized from 80% aqueous acetonitrile

Sources & evidence

ORD record
ord-4518b52dbc2e4e7383571d83f4b5ddca
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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