Benzene → HCID 131711104, compound

HRID 1448862Notes

Reaction equation

HRID 1448862 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][CH:10]=O)=[N+:2]=[N-:3].C1(C)C=C[C:15]([S:18](O)(=O)=O)=CC=1.[CH:23]1[CH:28]=[CH:27][C:26]([CH2:29][SH:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+].[CH:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O.C(OCC)(=O)C>[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][CH:10]([S:18][CH2:15][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[S:30][CH2:29][C:26]1[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=1)=[N+:2]=[N-:3]

Participants

8

Reactant 5

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 7509Benzyl mercaptanHCID 516892Sodium BicarbonateHCID 131711103HCID 131711103, compound

Product 1

HCID 131711104HCID 131711104, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 230 mg (1.45 mmole) of cis-3-azido-4-oxo-2-azetidineacetaldehyde, 20 mg of p-toluenesulfonic acid and 0.5 ml of benzylthiol in 25 ml of benzene and 5 ml of dimethylformamide was heated under reflux for 1 hour. After cooling, the mixture was shaken with ethyl acetate and 5% sodium bicarbonate, the organic phase washed with brine, dried and evaporated to dryness. Chromatography over silica gel with chloroform afforded 83 mg (13%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. washthe organic phase washed with brine
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f4ebfe12ac1f467d8b6ba88febe4d840
Source dataset
uspto-grants-1980_02
Patent number
US04187375

Reaction notes

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