Methanol → HCID 19849137, compound

HRID 1608318Notes

Reaction equation

HRID 1608318 reaction equation
S(Cl)(Cl)=[O:2].O[C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]([NH:12][CH2:13][C:14](O)=[O:15])[CH:9]=[CH:10][CH:11]=1.[CH3:20][OH:21]>>[CH3:20][O:21][C:14](=[O:15])[CH2:13][NH:12][C:8]1[CH:9]=[C:10]([OH:2])[CH:11]=[CH:6][C:7]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 19849124HCID 19849124, compound

Product 1

HCID 19849137HCID 19849137, compoundYield 97%

Procedure

Thionyl chloride 30.84 g (260 mM) was added dropwise with ice cooling to N-(hydroxy-2-nitrophenyl)-amino acetic acid 45.78 g (0.216 mole) dissolved in methanol 500 ml for 30 mins.; then the mixture was stirred at room temperature for 22 hours. The reaction mixture was filtered, the filtered material was washed with methanol and dried to obtain the yellow solid product. The above filtrate was concentrated in vacuo and the precipitated material was washed with chloroform and dried. The solid materials thus obtained were combined to obtain the product 47.5 g (yield: 97%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtered material was washed with methanol
  3. customdried
  4. customto obtain the yellow solid product
  5. concentrationThe above filtrate was concentrated in vacuo
  6. washthe precipitated material was washed with chloroform
  7. customdried
  8. customThe solid materials thus obtained

Sources & evidence

ORD record
ord-b16d1f33dace41308bfc5c75f0e3d8b7
Source dataset
uspto-grants-1989_09
Patent number
US04870175

Reaction notes

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