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2-Chloroethanol → 2-chloroethoxy-2-methyl-2H-indazole-3-sulfonamide

HRID 1378931
Notes
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Reaction equation

HRID 1378931 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[C:15]2[C:19]([CH:20]=[CH:21][CH:22]=1)=[N:18][N:17]([CH3:23])[C:16]=2[S:24]([NH2:27])(=[O:26])=[O:25].[Cl:28][CH2:29][CH2:30]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:28][CH2:29][CH2:30][O:13][C:14]1[C:15]2[C:19]([CH:20]=[CH:21][CH:22]=1)=[N:18][N:17]([CH3:23])[C:16]=2[S:24]([NH2:27])(=[O:26])=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 135829371HCID 135829371, compound

Product 1

HCID 867496182-chloroethoxy-2-methyl-2H-indazole-3-sulfonamideYield 26%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

3.8 g (22 mmol) of diethylazo dicarboxylate was added to a solution containing 5 g (22 mmol) of 4-hydroxy-2-methyl-2H-indazole-3-sulfonamide, 1.8 g (22 mmol) of 2-chloroethanol and 5.8 g (22 mmol) of triphenylphosphine in 50 ml of THF, and the mixture was stirred at room temperature for 20 hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, then concentrated and purified by column chromatography (hexane/ethyl acetate=2/1) to obtain 1.66 g (yield: 26%) of the desired product. Melting point: 177°-179° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. custompurified by column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ee91f44886684ab694d18aa5ab51fbbe
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05670452

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes