2-Methyl-2-oxazoline → N-Acetyl-4-S-cysteaminylphenol

HRID 1608463Notes

Reaction equation

HRID 1608463 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][N:6]=1.[SH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1>>[CH3:1][C:2]([NH:6][CH2:5][CH2:4][S:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 707132-Methyl-2-oxazolineHCID 2401474-Mercaptophenol

Product 1

HCID 124470N-Acetyl-4-S-cysteaminylphenolYield 87%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-methyl-2-oxazoline (16.9 mL, 0.197 mol) and 4-mercaptophenol (24.85 g, 0.197 mol) was heated under reflux (neat) for 2 h at about 130° C. under Ar (spontaneous heating occurred upon mixing). Upon cooling of the reaction mixture to 0° C., a white solid precipitated, which was collected and recrystallized from dilute EtOH to give a white product (36.2 g, 87%): mp 123°-125° C.; 1H NMR [(CD3)2 =O]δ6.99 (d,d, 4 H) , 3.50-2.60 (m, 5 H), 1.87 (s, 3 H); mass spectrum (EI) , m/e 211 (M+), (CI) m/e 212 (M+1). Anal. (C10H13NO2S) C,H,N.

Workup

  1. temperaturewas heated
  2. temperatureunder Ar (spontaneous heating occurred upon mixing)
  3. temperatureUpon cooling of the reaction mixture to 0° C.
  4. customa white solid precipitated
  5. customwhich was collected
  6. customrecrystallized from dilute EtOH

Sources & evidence

ORD record
ord-4927671710a048a99c2066b7900b5ad0
Source dataset
uspto-grants-1995_03
Patent number
US05395611

Reaction notes

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