Ethanol → Ethyl 4-(aminomethyl)benzoate--hydrogen chloride (1/1)

HRID 1692537Notes

Reaction equation

HRID 1692537 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O.[CH2:16](O)[CH3:17]>>[ClH:14].[CH2:16]([O:8][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH2:1])=[CH:11][CH:10]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 16236386Ethyl 4-(aminomethyl)benzoate--hydrogen chloride (1/1)

Procedure

20.0 g (132 mM) of 4-aminomethylbenzoic acid are suspended in 200 ml ethanol (EtOH) abs. and cooled with ice. 28.0 g (17 ml) (236 mM) thionylchloride are added drop by drop. The clear mixture is then refluxed for 3 hours. After cooling to room temperature, EtOH is evaporated. 50 ml of toluene/EtOH 1/1 are added and evaporated three times. The residue is dried to get 27 g of (1).

Workup

  1. temperatureand cooled with ice
  2. temperatureThe clear mixture is then refluxed for 3 hours
  3. customEtOH is evaporated
  4. addition50 ml of toluene/EtOH 1/1 are added
  5. customevaporated three times
  6. customThe residue is dried

Sources & evidence

ORD record
ord-7a93cf58ca3c4cdd854f76ca7d53162b
Source dataset
uspto-grants-2012_04
Patent number
US08158438B2

Reaction notes

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