Water → HCID 15713225, compound

HRID 1195921Notes

Reaction equation

HRID 1195921 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29]([OH:31])=O.Cl.[CH3:33][NH:34][OH:35].O>C(Cl)Cl>[OH:35][N:34]([CH3:33])[C:29](=[O:31])[CH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:15]1[C:14]([Cl:13])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:20]

Participants

6

Reactant 4

HCID 962WaterHCID 3033DiclofenacHCID 682631,1'-CarbonyldiimidazoleHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 15713225HCID 15713225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1'-Carbonyl-diimidazole (5.5 g; 34 mmol) is slowly added to a warm solution of 2-[(2,6-dichlorophenyl)-amino]-benzeneacetic acid (6.5 g; 22 mmol) in CH2Cl2 (600 mL) and stirred at room temperature for 2.0 hours when a clear solution is formed. N-Methylhydroxylamine hydrochloride (5.5 g; 66 mmol) is slowly added to the solution and the mixture stirred at room temperature for 48 hours. It is decomposed with water, extracted with CH2Cl2 and dried over Na2SO4. The solvent is evaporated off and the residue flash chromatographed over silica gel (250 g) using 10% EtOH-CH2Cl2 as eluant to give the pure product as white solid which is recrystallized from toluene-CH2Cl2. Yield 2.95 g (41.2%); mp 135°-138° C.

Workup

  1. customis formed
  2. stirringthe mixture stirred at room temperature for 48 hours
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customThe solvent is evaporated off
  6. customthe residue flash chromatographed over silica gel (250 g)

Sources & evidence

ORD record
ord-726b0532131d44d4baa6b9abf7cf945c
Source dataset
uspto-grants-1992_05
Patent number
US05112868

Reaction notes

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