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Dichloromethane → HCID 58941813, compound

HRID 2097655
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Reaction equation

HRID 2097655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][OH:18])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(Cl)Cl>C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH:17]=[O:18])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 58941855N-(3-chloro-4-fluorophenyl)-4-(hydroxymethyl)-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 58941813HCID 58941813, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of N-(3-chloro-4-fluorophenyl)-4-(hydroxymethyl)-1,2,5-oxadiazole-3-carboxamide (8.50 g, 31.3 mmol), Dess-Martin periodinane (14.6 g, 34.4 mmol) and DCM (400 mL) was stirred at 25° C. for 3 h. The reaction was diluted with a saturated sodium bicarbonate solution and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-968e50d692504bf28cc95c45f216293d
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450351B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes