Lithium aluminum hydride → Thiophene-2-sulfonic acid (2,4-difluoro-3-hydroxymethyl-phenyl)-amide

HRID 1261050Notes

Reaction equation

HRID 1261050 reaction equation
C([O:3][C:4](=O)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[C:6]=1[F:21])C.[AlH4-].[Li+]>O1CCCC1>[F:21][C:6]1[C:5]([CH2:4][OH:3])=[C:10]([F:11])[CH:9]=[CH:8][C:7]=1[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 595067472,6-Difluoro-3-(thiophene-2-sulfonylamino)-benzoic acid ethyl ester

Product 1

HCID 58087783Thiophene-2-sulfonic acid (2,4-difluoro-3-hydroxymethyl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,6-difluoro-3-(thiophene-2-sulfonylamino)-benzoic acid ethyl ester (510, 1.6 g, 3.5 mmol) in tetrahydrofuran (25.0 mL) was added lithium tetrahydroaluminate (1.00 M in tetrahydrofuran, 8.08 mL, 8.08 mmol) under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature for 8 hours, followed by addition of 10 g of NaSO4.10H2O. After 12 hours, the reaction was filtered, concentrated and purified with silica gel column chromatography eluting with 5% methanol in methylene chloride to give a white solid (511, 300.0 mg, 21.0%).

Workup

  1. waitAfter 12 hours
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 5% methanol in methylene chloride
  6. customto give a white solid (511, 300.0 mg, 21.0%)

Sources & evidence

ORD record
ord-1c44fe2addeb4df88b7328640729b953
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

Loading…