Sodium Hydroxide → HCID 20478031, compound

HRID 904912Notes

Reaction equation

HRID 904912 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28]CC)=[O:27])=[CH:22][CH:21]=2)=[O:18])[CH2:11][CH2:12][N:13]=1.[OH-].[Na+]>Cl>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([OH:28])=[O:27])=[CH:24][CH:25]=2)=[O:18])[CH2:11][CH2:12][N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 20478043HCID 20478043, compound

Product 1

HCID 20478031HCID 20478031, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

22.6 g of the 1-[2-[2-(2-chlorophenyl)-2-imidazolin-1-yl]-ethyl]-3-(4-ethoxycarbonyl-phenyl)-urea hydrochloride obtained according to Example 19 are dissolved in 900 ml of 95% alcohol and the base is liberated with 50 ml of 1 N sodium hydroxide solution. After adding 200 ml of 2 N sodium hydroxide solution, the mixture is stirred overnight. It is then neutralised with 200 ml of 2 N hydrochloric acid and slightly acidified with 51 ml of 1 N hydrochloric acid. The resulting mixture is evaporated to dryness in a rotary evaporator and the residue is twice boiled thoroughly with 100 ml of alcohol. The residue consists of sodium chloride; after substantial concentration, the solution yields crystalline 1-[2-[2-(2-chlorophenyl)-2-imidazolin-1-yl]-ethyl]-3-(4-carboxyphenyl)-urea hydrochloride, which is recrystallised from methanol/isopropanol and then melts at 240°-242° with decomposition.

Workup

  1. customThe resulting mixture is evaporated to dryness in a rotary evaporator
  2. concentrationafter substantial concentration

Sources & evidence

ORD record
ord-048a896614f34df39b4bb37d9bd67c7b
Source dataset
uspto-grants-1983_12
Patent number
US04420619

Reaction notes

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