Sulfuric Acid → HCID 86673620, compound

HRID 1616983Notes

Reaction equation

HRID 1616983 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[CH:7][CH:6]=1)[C:2]#[CH:3].[OH:15][S:16]([OH:19])(=[O:18])=[O:17]>>[S:16]([OH:19])([OH:18])(=[O:17])=[O:15].[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[C:2]#[CH:3]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 60643689HCID 60643689, compound

Product 1

HCID 86673620HCID 86673620, compoundYield 68%

Procedure

A solution of N-(4-(propargyloxy)phenyl)acetamide 5 (650 mg, 3.44 mmol) in 4 M H2SO4 (10 mL) was stirred under reflux for 3 h. The generated white crystals were filtrated and washed with diethyl ether to give 6 (577 mg, 68%). 1H NMR (300 MHz, DMSO-d6): δ 8.18 (br, 2H), 6.97-6.90 (m, 4H), 4.73 (d, J=3.0 Hz, 2H), 3.55 (t, J=3.0 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 153.92, 134.71, 120.94, 117.17, 80.61, 79.20, 57.06. HRMS: calcd for C9H10NO (MH+) 148.0757. found 148.0754.

Workup

  1. temperatureunder reflux for 3 h
  2. filtrationThe generated white crystals were filtrated
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6dcae9a3865941acb1bfe9fc96124924
Source dataset
uspto-grants-2014_07
Patent number
US08765920B2

Reaction notes

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