Water → HCID 15713224, compound

HRID 2166106Notes

Reaction equation

HRID 2166106 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([OH:19])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[O:33]([NH2:35])[CH3:34].O>C(Cl)Cl>[CH3:34][O:33][NH:35][C:17](=[O:19])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 3033DiclofenacHCID 682631,1'-CarbonyldiimidazoleHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 15713224HCID 15713224, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A warm solution of 2-[(2,6-dichlorophenyl)amino]-benzeneacetic acid (2.03 g; 7 mmol) in CH2Cl2 (100 mL) is treated with 1,1'-carbonyl-diimidazole (1.75 g; 11 mmol) and the mixture is stirred at room temperature for 5.0 minutes when a clear solution is obtained. The solution is then treated with methoxylamine hydrochloride (1.50 g; 18 mmol) and the reaction mixture stirred at room temperature for 108 hours. It is then decomposed with water, extracted with CH2Cl2, dried over Na2SO4 and then evaporated to dryness to give a solid. Fractional recrystallization of the crude product from a mixture of toluene-CH2Cl2 gives off-white crystalline solid (1.27 g; 55.8%); mp 177°-178° C.

Workup

  1. customis obtained
  2. stirringthe reaction mixture stirred at room temperature for 108 hours
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customto give a solid
  7. customFractional recrystallization of the crude product
  8. additionfrom a mixture of toluene-CH2Cl2
  9. customgives off-white crystalline solid (1.27 g; 55.8%)

Sources & evidence

ORD record
ord-da6dc012339447fb9fa911ac81b7ba3e
Source dataset
uspto-grants-1990_07
Patent number
US04943587

Reaction notes

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