Sodium Chloride → (2-Chloroacetamido) (2-benzoyl-4-nitrophenylazo)-malonic acid diethyl ester

HRID 2399145Notes

Reaction equation

HRID 2399145 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[N:19]([O-])=O.[Na+].[CH2:23]([O:25][C:26](=[O:38])[CH:27]([NH:33][C:34](=[O:37])[CH2:35][Cl:36])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:24].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>C(O)(=O)C.Cl.CC(C)=O.O.C1C=CC=CC=1>[CH2:23]([O:25][C:26](=[O:38])[C:27]([NH:33][C:34](=[O:37])[CH2:35][Cl:36])([N:19]=[N:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4](=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:24]

Participants

11

Reactant 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 156812-Amino-5-nitrobenzophenoneHCID 243559Diethyl (2-chloroacetamido)propanedioateHCID 23668193Sodium Nitrite

Product 1

HCID 54206090(2-Chloroacetamido) (2-benzoyl-4-nitrophenylazo)-malonic acid diethyl ester

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 241BenzeneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 20 g (0.826 mole) of 2-amino-5-nitro benzophenone (cp. Ullmann, Ber. 31, 1965) in 400 ml of glacial acetic acid and 20 ml of conc. hydrochloric acid is diazotised at 20°-25°, with stirring, with 16.5 ml (0.826 mole) of aqueous sodium nitrite solution. To the obtained diazonium salt solution there are added 400 g of ice, and rapidly dropwise a solution of 174 g (0.69 mole) of (2-chloroacetamido)-malonic acid diethyl ester [cp. Ajay Kumar Bose, J. Indian Chem. Soc. 31, 108-110 (1954)] in 400 ml of acetone. A solution of 114 g (0.826 mole) of potassium carbonate in 250 ml of water is subsequently added dropwise at 5°-10° within 20 minutes; stirring is continued for an hour, and benzene and saturated sodium chloride solution added. The benzene solution is separated, washed repeatedly with a mixture of saturated sodium chloride solution and 5% sodium bicarbonate solution until free from acid, dried over sodium sulphate and concentrated by evaporation, whereby crude (2-chloroacetamido) (2-benzoyl-4-nitrophenylazo)-malonic acid diethyl ester is obtained.

Workup

  1. customis diazotised at 20°-25°
  2. waitis continued for an hour
  3. customThe benzene solution is separated
  4. washwashed repeatedly with a mixture of saturated sodium chloride solution and 5% sodium bicarbonate solution until free from acid
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ac86657641714191b523ee20892623e1
Source dataset
uspto-grants-1977_05
Patent number
US04027029

Reaction notes

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