Hydrochloric Acid → HCID 20277958, compound

HRID 1248439Notes

Reaction equation

HRID 1248439 reaction equation
[NH:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:12]([Cl:15])(=[O:14])[CH3:13]>C(#N)C>[ClH:15].[C:12]([O:10][CH2:9][CH2:8][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 31235N-(2-Hydroxyethyl)aniline

Product 1

HCID 20277958HCID 20277958, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

2-Anilinoethanol (137 g, 1.0 mol) was mixed with acetonitrile (300 ml) and concentrated hydrochloric acid (100 ml), and the reaction mixture was evaporated to dryness. The residue was dissolved in acetonitrile (1000 ml); acetyl chloride (89 ml, 1.25 mol) was added and the reaction mixture was stirred at room temperature (22° C.) for 16 hours. The mixture was evaporated to dryness under reduced pressure and the resulting solid was triturated with ethyl ether (1000 ml). The solid was removed by filtration and dried to yield 197 g (91.3%) of product.

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in acetonitrile (1000 ml)
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe resulting solid was triturated with ethyl ether (1000 ml)
  5. customThe solid was removed by filtration
  6. customdried

Sources & evidence

ORD record
ord-b70871a7311040b79eeee606295ab1b4
Source dataset
uspto-grants-1985_06
Patent number
US04524122

Reaction notes

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