Acetyl chloride → HCID 15289370, compound

HRID 399734Notes

Reaction equation

HRID 399734 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[C:11]([Cl:12])=[C:10]([NH:13][CH2:14][CH2:15][OH:16])[C:9]([Cl:17])=[C:8]([Cl:18])[N:7]=1>C(O)(=O)C>[Cl:5][C:6]1[C:11]([Cl:12])=[C:10]([NH:13][CH2:14][CH2:15][O:16][C:1](=[O:3])[CH3:2])[C:9]([Cl:17])=[C:8]([Cl:18])[N:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 18945007HCID 18945007, compound

Product 1

HCID 15289370HCID 15289370, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 34.4 ml (490 mmol) acetyl chloride in 250 ml glacial acetic acid was added dropwise to a suspension of 105 g (380 mmol) 2-(2,3,5,6-tetrachloropyridin-4-ylamino)-ethanol in 860 ml glacial acetic acid. During this the temperature increased to 40° C. After 2 h it was poured onto ice water, filtered, washed with water, the residue was dissolved in 500 ml ethyl acetate, dried over sodium sulfate, filtered and the solvent was removed in a vacuum. 112 g (93%) acetic acid-2(2,3,5,6-tetrachloropyridin-4-ylamino)-ethyl ester was obtained and was reacted without further purification. MS (m/e)=316.

Workup

  1. additionAfter 2 h it was poured onto ice water
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionthe residue was dissolved in 500 ml ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-6184c84ef87547ae95fb6f7699dab4d2
Source dataset
uspto-grants-1998_10
Patent number
US05824679

Reaction notes

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