Ethyl Acetate → HCID 15980787, compound

HRID 859170Notes

Reaction equation

HRID 859170 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([S:17][CH2:18][C:19]([OH:21])=[O:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]O.C(OCC)(=O)C>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][O:20][C:19](=[O:21])[CH2:18][S:17][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 680083-Fluorobenzylic alcoholHCID 10018018HCID 10018018, compound

Product 1

HCID 15980787HCID 15980787, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of [5-(4-fluorophenylcarbamoyl)pyridin-2-ylsulfanyl]acetic acid (0.030 g, 0.10 mmole), 3-fluorobenzyl alcohol (0.10 mL, 1.0 mmol), and sulfuric acid (1 drop) in toluene (5 mL) was heated at reflux. After 2 h the reaction mixture was poured into ethyl acetate and washed with saturated sodium bicarbonate and dried over sodium sulfate. Removal of the solvents provided a solid. Purification by trituration using ethyl acetate/hexanes gave 0.011 g (27%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s 1H); 8.86 (m, 1H); 8.12 (m, 1H); 7.74 (m, 2H); 7.51 (m, 1H); 7.35 (m, 1H); 7.15 (m, 5H); 5.16 (m, 2H), 4.18 (m, 2H); MS (EI) m/z 413.05 (M−H)−.

Workup

  1. temperatureat reflux
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvents
  5. customprovided a solid
  6. customPurification by trituration

Sources & evidence

ORD record
ord-79bd3deb4819490da6d33874e720da67
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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