Hydrochloric Acid → HCID 20481527, compound

HRID 1649030Notes

Reaction equation

HRID 1649030 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:17])[C:8]([C:14](=[O:16])[CH3:15])=[CH:9][C:10]=1[C:11](=[O:13])[CH3:12])(=O)[CH3:2].[H-].[Na+].C(I)C.Cl>CN1CCCC1=O.C(O)C>[C:11]([C:10]1[CH:9]=[C:8]([C:14](=[O:16])[CH3:15])[C:7]([OH:17])=[CH:6][C:5]=1[NH:4][CH2:1][CH3:2])(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2775200N-(2,4-diacetyl-5-hydroxyphenyl)acetamide

Product 1

HCID 20481527HCID 20481527, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

3-Acetamido-4,6-diacetylphenol (0.01 mole) in N-methylpyrrolidone (NMP) (20 ml) was added to a cooled (<5° C.), stirred suspension of sodium hydride (0.022 mole) in NMP (5 ml). After 15 minutes the mixture was treated with ethyliodide (0.019 mole). After two hours at <5° C., the mixture was acidified with ethanol/conc. HCl (1:1, 20 ml) and heated to reflux for 21/2 hours. The mixture was allowed to cool and the crystalline subtitle compound isolated by filtration. Yield 63%, mp 103°-104° C.

Workup

  1. temperaturea cooled (<5° C.)
  2. temperatureto reflux for 21/2 hours
  3. temperatureto cool

Sources & evidence

ORD record
ord-8fe27a4e3e804625b2c1e7ebcdbdf1f6
Source dataset
uspto-grants-1983_11
Patent number
US04414416

Reaction notes

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