Thionyl Chloride → alpha-Sulfo-alpha-(p-nitrophenyl)acetic acid chloride

HRID 462261Notes

Reaction equation

HRID 462261 reaction equation
S(Cl)([Cl:3])=O.[S:5]([CH:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:10](O)=[O:11])([OH:8])(=[O:7])=[O:6]>CN(C)C=O.CCOCC>[S:5]([CH:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:10]([Cl:3])=[O:11])([OH:8])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20449064alpha-Sulfo-alpha-(p-nitrophenyl)acetic acid

Product 1

HCID 20556789alpha-Sulfo-alpha-(p-nitrophenyl)acetic acid chlorideYield 81.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

6.58 Grams (5.7 × 10-2M) of thionyl chloride, 2 ml. of ether and 2 drops of dimethylformamide were added to 1.5 g. (5.7 × 10-3M) of α-sulfo-α-(p-nitrophenyl)acetic acid to allow to react for 14.5 hours at room temperature. The reaction product was subjected to the evaporation to dryness under reduced pressure to obtain a crude desired product. Yield 81.3%.

Workup

  1. customto react for 14.5 hours at room temperature
  2. customThe reaction product was subjected to the evaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-a35e28ba5d044c3bbf73d559348e2e04
Source dataset
uspto-grants-1977_12
Patent number
US04065619

Reaction notes

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