Acetic Anhydride → N-(4-ethynylphenyl)acetamide

HRID 1271041Notes

Reaction equation

HRID 1271041 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[CH:2].[C:10](OC(=O)C)(=[O:12])[CH3:11]>ClCCl>[C:10]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([C:1]#[CH:2])=[CH:4][CH:5]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 37600254-Ethynylaniline

Product 1

HCID 11412536N-(4-ethynylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of 4-ethynylaniline and 2.4 mL of acetic anhydride in 5.0 mL of dichloromethane was stirred at room temperature for 18 hours. The solution was evaporated in vacuo at 40° C. The resulting semi solid mixture was suspended in hexanes and filtered. The hexanes filtrate was washed twice with water and dried over sodium sulfate. After filtering it was combined with the hexanes insoluble residue, dissolved in dichloromethane and purified by column chromatography in the same solvent to yield 0.96 g of 1-acetamido-4-ethynylbenzene.

Workup

  1. customThe solution was evaporated in vacuo at 40° C
  2. filtrationfiltered
  3. washThe hexanes filtrate was washed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering it
  6. dissolutiondissolved in dichloromethane
  7. custompurified by column chromatography in the same solvent

Sources & evidence

ORD record
ord-e2addbc025f34d739e94072a82f5fbda
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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