Ethanol → 6415-38-9

HRID 2054133Notes

Reaction equation

HRID 2054133 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)C.C(O[N:22]=O)CC(C)C>C(OCC)C>[S:1](=[O:3])(=[O:2])([O-:5])[O-:4].[C:7]1([N+:6]#[N:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1([N+:6]#[N:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6115AnilineHCID 8053Isoamyl Nitrite

Product 1

HCID 127442706415-38-9

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Concentrated sulfuric acid (50 mL, 96%) was slowly dropped into a solution of aniline (30 g. 0.32 mol) ill ethanol (280 mL) until the white precipitate newly formed disappeared again at 0-5° C. To this mixture, isoamylnitrite (40 g, 0.34 mol) was slowly added with stirring. An equal volume of ethyl ether was added to precipitate the product. The mixture was filtered and the residue washed with ethanol:ether (1:1, v/v) to provide a crude greenish solid of benzenediazonium sulfuric acid salt for the following reaction.

Workup

  1. customnewly formed
  2. customdisappeared again at 0-5° C
  3. customto precipitate the product
  4. filtrationThe mixture was filtered
  5. washthe residue washed with ethanol:ether (1:1

Sources & evidence

ORD record
ord-c83788f2c1bd45cd875e49f8950ebd2f
Source dataset
uspto-grants-2008_02
Patent number
US07329651B2

Reaction notes

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