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(Diethylamino)sulfur trifluoride → HCID 86600991, compound

HRID 1351294
Notes
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Reaction equation

HRID 1351294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[S:15][C:16]([Br:19])=[CH:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:28][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][N:10]([CH3:20])[S:11]([C:14]1[S:15][C:16]([Br:19])=[CH:17][CH:18]=1)(=[O:13])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 21098651HCID 21098651, compound

Product 1

HCID 86600991HCID 86600991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromothiophene-2-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 71) (210 mg) in dichloromethane (2 mL) was added dropwise (diethylamino)sulfur trifluoride (DAST) (0.1 mL) at −70° C., After gradually warming slowly to 0° C. over 1.5 hours, an aqueous solution of saturated sodium bicarbonate was added, and the solution was extracted with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and was dried with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (169 mg) was obtained as a pale yellow oily substance.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washAfter the organic layer was washed with saturated sodium chloride water
  3. dry with materialwas dried with anhydrous sodium sulfate
  4. customthe residue that was obtained
  5. customupon removing the solvent
  6. customby evaporation
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-982204c5878d4e05ac3ec4b6c380befd
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217723B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes