Hydrochloric Acid → HCID 57036282, compound

HRID 1980561Notes

Reaction equation

HRID 1980561 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].Cl.[N:21]([O-])=O.[Na+].[CH3:25][O:26][C:27](=[O:39])[CH:28]([NH:33][C:34](=[O:38])[CH:35]([Cl:37])[CH3:36])[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CC(C)=O.C(OCC)(=O)C>[CH3:32][O:31][C:29](=[O:30])[C:28]([N:21]=[N:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:19])([NH:33][C:34](=[O:38])[CH:35]([Cl:37])[CH3:36])[C:27]([O:26][CH3:25])=[O:39]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13519230Ethyl (2-aminophenyl)phenylcarbamateHCID 13519319HCID 13519319, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57036282HCID 57036282, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 26.20 g (0.102 mol) of the (2-aminophenyl)-phenylcarbamic acid ethyl ester prepared according to Example (1b) in 246 ml of glacial acetic acid and 62 ml of concentrated hydrochloric acid is diazotised at 0°-5° over a period of 20 minutes with 20.4 ml (0.102 mol) of a 5-molar sodium nitrite solution. 60 g of ice are added to the resulting diazonium salt solution, and then 24.23 g (0.102 mol) of (2-chloropropionamido)-malonic acid dimethyl ester in 243 ml of acetone are then quickly added dropwise. Then, at 0°-5°, 500 ml of a saturated potassium carbonate solution are added over a period of 30 minutes, the pH value finally being 6. After stirring for a further one hour at 0°-5, 300 ml of ethyl acetate are added, the organic phase is separated off and the aqueous phase extracted once more with ethyl acetate. The combined organic extracts are washed four times with water and twice with saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in vacuo, yielding the orange-colored [2-(N-ethoxycarbonylphenylamino)-phenylazo]-(2-chloropropionamido)-malonic acid dimethyl ester which is of honey-like consistency. It can be used in the next stage without further purification.

Workup

  1. additionare added
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase extracted once more with ethyl acetate
  4. washThe combined organic extracts are washed four times with water
  5. dry with materialtwice with saturated sodium chloride solution, dried over sodium sulphate
  6. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-c8858ef943884e6a840b9e59d1f01455
Source dataset
uspto-grants-1985_04
Patent number
US04510141

Reaction notes

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