Diethanolamine → N,N-bis(2-hydroxyethyl)-2-methoxy-3,6-dichlorobenzamide

HRID 485194

Reaction equation

HRID 485194 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[CH3:15][O:16][C:17]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([Cl:27])[C:18]=1[C:19](Cl)=[O:20]>C1(C)C=CC=CC=1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[C:19](=[O:20])[C:18]1[C:22]([Cl:27])=[CH:23][CH:24]=[C:25]([Cl:26])[C:17]=1[O:16][CH3:15]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 82609Benzoyl chloride, 3,6-dichloro-2-methoxy-

Product 1

HCID 14156697N,N-bis(2-hydroxyethyl)-2-methoxy-3,6-dichlorobenzamideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diethanolamine (11 grams; 0.105 mol), triethylamine (12 grams) and toluene (100 ml) were placed in a 250 ml, 3-necked glass reaction flask equipped with stirrer, thermometer and reflux condenser. 2-methoxy-3,6-dichlorobenzoic acid chloride (23.9 grams; 0.1 mol) in toluene (25 ml) were added to the reaction mixture by means of an addition funnel. The reaction mixture was stirred for two hours and then filtered. The recovered solid material was heated in ethyl acetate and filtered. Toluene was added to the oily residue, heated to dissolve the oil and cooled. The desired product first formed as an oil and then crystalized. The product weighed 23.6 grams representing a yield of 76%.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and reflux condenser
  3. filtrationfiltered
  4. temperatureThe recovered solid material was heated in ethyl acetate
  5. filtrationfiltered
  6. additionToluene was added to the oily residue
  7. temperatureheated
  8. dissolutionto dissolve the oil
  9. temperaturecooled

Sources & evidence

ORD record
ord-4c92cc8344354feabf2e3358cf30cd62
Source dataset
uspto-grants-1985_08
Patent number
US04536210

Linked notes

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