Water → HCID 20220832, compound

HRID 980959Notes

Reaction equation

HRID 980959 reaction equation
O.[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:5])[CH:3]=[O:4].[CH3:17][S:18][CH:19]1[NH:22][C:21](=[O:23])[CH2:20]1.O>C1C=CC=CC=1>[OH:4][CH:3]([N:22]1[CH:19]([S:18][CH3:17])[CH2:20][C:21]1=[O:23])[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 126772484-(Methylsulfanyl)azetidin-2-oneHCID 21934455p-Nitrobenzyl glyoxylate hydrate

Product 1

HCID 20220832HCID 20220832, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Nitrobenzyl glyoxylate monohydrate (1.11 g, 4.87 mmoles) was added to a solution of 4-methylthio-2-azetidinone (570 mg, 4.87 mmoles) in benzene (30 ml) and the resulting solution was heated, whilst the water produced was removed by azeotropic distillation. After the water had been distilled off completely, the mixture was concentrated and heated at a bath temperature of 100°-110° C. for 12 hours. The solvent was then distilled off under reduced pressure to give 1.69 g of the desired compound as a viscous oil. This product may be employed in subsequent reactions without purification, although it contains a small amount of the starting compound.

Workup

  1. customproduced
  2. customwas removed by azeotropic distillation
  3. distillationAfter the water had been distilled off completely
  4. concentrationthe mixture was concentrated
  5. temperatureheated at a bath temperature of 100°-110° C. for 12 hours
  6. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-c4b35f144882476cb8d03696e23ab9fc
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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