Ammonia → HCID 20085028, compound

HRID 1609372Notes

Reaction equation

HRID 1609372 reaction equation
Cl[CH2:2][N:3]([C:10](=[O:13])[CH2:11][Cl:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N.[CH2:15]([OH:17])[CH3:16]>>[CH2:15]([O:17][CH2:2][N:3]([C:10](=[O:13])[CH2:11][Cl:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:16]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 702Ethanol3×HCID 12524057HCID 12524057, compound

Product 1

HCID 20085028HCID 20085028, compound

Procedure

About 2208 g (48 moles) of anhydrous ethanol was added to the reaction mixture containing the N-chloromethyl-α-chloroacetanilide intermediate. The addition of ethanol to the haloacetanilide mixture was done over 40 minutes at temperatures ranging from 45°-84° C. At the end of the ethanol addition, about 66.3 g (3.9 moles) of gaseous ammonia was introduced to the reaction mixture through a dip tube at about 50°-60° C. When the pH of the reaction mixture was about 8-9, the addition of ammonia was stopped and the reaction was considered complete. This reaction gave a 98.6% conversion of the haloacetanilide intermediate to the N-ethoxymethyl-2-chloroacetanilide.

Workup

  1. customranging from 45°-84° C
  2. additionwas introduced to the reaction mixture through a dip tube at about 50°-60° C

Sources & evidence

ORD record
ord-66e95cb1d1fd44bd8fca5b1507244a75
Source dataset
uspto-grants-1995_03
Patent number
US05399759

Reaction notes

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