2,6-Dichloroaniline → HCID 54158568, compound

HRID 437979Notes

Reaction equation

HRID 437979 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C(=O)([O-])O.[Na+].[CH3:15][O:16][C:17](=[O:21])[CH:18](Br)[CH3:19]>O>[CH3:15][O:16][C:17](=[O:21])[CH:18]([NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9])[CH3:19]

Participants

5

Reactant 3

HCID 118462,6-DichloroanilineHCID 95576Methyl 2-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 54158568HCID 54158568, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40.5 g of 2,6-dichloroaniline, 21 g of sodium hydrogen carbonate and 84 ml of DL-α-bromopropionic acid methyl ester are stirred in a sulphonating flask for 2 days at 140° bath temperature. After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The combined ethyl acetate fractions are extracted once with saturated sodium chloride solution, dried over sodium sulphate and concentrated in a rotary evaporator. The excess α-bromopropionic acid methyl ester is recovered in a water-jet vacuum. The darkly coloured residue remaining is fractionally distilled in high vacuum. There is obtained 23.6 g of α-(2,6-dichloroanilino)-propionic acid methyl ester; b.p. 85°-87°/0.001 Torr.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate fractions are extracted once with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in a rotary evaporator
  6. customThe excess α-bromopropionic acid methyl ester is recovered in a water-jet vacuum
  7. distillationThe darkly coloured residue remaining is fractionally distilled in high vacuum

Sources & evidence

ORD record
ord-546885e601fa481fa4e8006af24433e9
Source dataset
uspto-grants-1977_06
Patent number
US04032657

Reaction notes

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