Hydrochloric Acid → 4-(Chloromethyl)-N-(2-hydroxy-5-methylphenyl)benzamide

HRID 875309Notes

Reaction equation

HRID 875309 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14].[Cl:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.Cl>COCCO.O>[Cl:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:6][C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[OH:14])=[O:22])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72642-Amino-4-methylphenolHCID 701364-(Chloromethyl)benzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 867098014-(Chloromethyl)-N-(2-hydroxy-5-methylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent2×

Procedure

With stirring, 37.52 g (446.6 mmol) of sodium bicarbonate were added to 50 g (406 mmol) of 2-amino-4-methylphenol in 250 ml of 2-methoxyethanol. 84.4 g (446.6 mmol) of 4-chloromethylbenzoyl chloride, dissolved in 250 ml of 2-methoxyethanol, were then added dropwise to the solution over 15 min. During this time, an increase in reaction temperature of from room temperature to 40° C. was observed. After 4 hours of stirring, 1 liter of water and 10 ml of concentrated hydrochloric acid were added to the reaction mixture. The crystals formed were filtered off and dried under reduced pressure. This gave 116 g of the target compound which were reacted further without further purification.

Workup

  1. additionwere then added dropwise to the solution over 15 min
  2. temperatureDuring this time, an increase in reaction temperature of from room temperature to 40° C.
  3. stirringAfter 4 hours of stirring
  4. customThe crystals formed
  5. filtrationwere filtered off
  6. customdried under reduced pressure
  7. customThis gave 116 g of the target compound which were reacted further without further purification

Sources & evidence

ORD record
ord-3a44724a1ad74897bc45aeeb4384d68e
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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