Pyridine → HCID 20397536, compound

HRID 462844Notes

Reaction equation

HRID 462844 reaction equation
[C:1]([CH2:20][CH2:21][S:22][CH2:23][CH2:24][OH:25])([C:4]([C:7]([C:10]([C:13]([C:16]([F:19])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>>[C:26]([O:25][CH2:24][CH2:23][S:22][CH2:21][CH2:20][C:1]([F:3])([F:2])[C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([F:12])([F:11])[C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])(=[O:28])[CH3:27]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13859687HCID 13859687, compound2×

Product 1

HCID 20397536HCID 20397536, compound

Procedure

C6F13CH2CH2SCH2CH2OH (40.1 g, 0.094 mole, undistilled), acetic anhydride (16.2 g, 0.15 mole) and pyridine (0.98 g, 12.4 mmole) was heated at 65°-66° for 4 hours and 89° for 17 hours under total reflux. A sample after 4 hours showed incomplete reaction and after 17 hours, only a trace of C6F13CH2CH2SCH2CH2OH was present (GC analysis). The product was washed with saturated sodium bicarbonate (20 ml), extracted into ether, dried and the solvent removed by distillation; wt. 47.77 g. Total product was 49.3 g, 100% of theory. NMR was consistent for structure: proton resonances at 2.03 ppm, 3 protons, s, CH3 ; at 2.42 ppm, multiplet, 2 protons, CH2A ; at 2.78 ppm, multiplet, 4 protons, CH2A ; at 2.78 ppm, multiplet, 4 protons, CH2B and CH2C ; and at 4.24 ppm, t, 2 protons CH2D for C6F13CH2ACH2BSCH2CCH2DO2CCH3.

Workup

  1. customreaction
  2. waitafter 17 hours
  3. washThe product was washed with saturated sodium bicarbonate (20 ml)
  4. extractionextracted into ether
  5. customdried
  6. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-d934234bde494761b2b28b3665bb994e
Source dataset
uspto-grants-1985_05
Patent number
US04517384

Reaction notes

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