Formaldehyde → HCID 18940317, compound

HRID 355657Notes

Reaction equation

HRID 355657 reaction equation
Cl.[NH2:2][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=O.C=O.C1(C)C=C[C:27]([S:30](O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.C(N(CC)CC)C>[C:13]1([CH:18]2[S:30][CH2:27][N:2]([C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]2=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 51275252-Mercaptophenylacetic acidHCID 22343822Ethyl 2-amino-2-methylpropanoate hydrochloride

Product 1

HCID 18940317HCID 18940317, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (3 g) was added to a suspension of ethyl 2-aminoisobutyrate hydrochloride (5 g) in toluene (60 mL) at room temperature. 2-Mercaptophenylacetic acid (6.44 g) was added to the mixture, which was then stirred at room temperature. After 10 minutes, a 35% formaldehyde aqueous solution (2.61 g) was added dropwise to the mixture. After the addition was completed, a catalytic amount of p-toluenesulfonic acid was added, and the mixture was allowed to react under heating at reflux for 4 hours, while water generated was excluded by azeotropic distillation from the reaction system. The reaction mixture was cooled to room temperature, to which ethyl acetate was added, and was then washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled under reduced pressure to give 5.49 g of the title compound as viscous oil.

Workup

  1. additionAfter the addition
  2. customto react
  3. temperatureunder heating
  4. distillationgenerated was excluded by azeotropic distillation from the reaction system
  5. temperatureThe reaction mixture was cooled to room temperature, to which ethyl acetate
  6. additionwas added
  7. washwas then washed with a saturated sodium hydrogencarbonate aqueous solution
  8. dry with materiala saturated aqueous sodium chloride and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-1dba1b63eb9a4834be0247feb505f5fe
Source dataset
uspto-grants-1998_11
Patent number
US05834401

Reaction notes

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