Chloroacetyl chloride → HCID 21493342, compound

HRID 1973229Notes

Reaction equation

HRID 1973229 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([O:9][CH2:10][CH3:11])[N:3]=1.C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>CCOCC>[Cl:1][C:2]1[C:7]([NH:8][C:21](=[O:22])[CH2:20][Cl:19])=[CH:6][CH:5]=[C:4]([O:9][CH2:10][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 214933322-Chloro-6-ethoxypyridin-3-amine

Product 1

HCID 21493342HCID 21493342, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-chloro-3-amino-6-ethoxypyridine (17 grams) in ether (200 ml), and triethylamine (10 grams) are placed in a glass reaction flask equipped with stirrer, thermometer and addition funnel. The mixture is cooled to about 0° to 10° C and a solution of chloroacetyl chloride (11.3 grams) in ether (40 ml) is slowly added thereto over a period of about 30 minutes resulting in the formation of a precipitate. The precipitate is recovered by filtration and is washed first with aqueous sodium bicarbonate and then with water. The washed product is then dried to yield the desired product N-(2-chloro-6-ethoxy-3-pyridyl)-α-chloroacetamide.

Workup

  1. customequipped with stirrer
  2. additionthermometer and addition funnel
  3. temperatureThe mixture is cooled to about 0° to 10° C
  4. customover a period of about 30 minutes resulting in the formation of a precipitate
  5. filtrationThe precipitate is recovered by filtration
  6. washis washed first with aqueous sodium bicarbonate
  7. customThe washed product is then dried

Sources & evidence

ORD record
ord-eeef1d77c277444c9a240341e24c35de
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Reaction notes

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