1-Chloroethyl chloroformate → HCID 68853669, compound

HRID 227298Notes

Reaction equation

HRID 227298 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[O:23][CH3:24])[N:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:18]=[C:17]3[S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:40]C(OC(Cl)=O)C>ClCCCl>[ClH:40].[CH3:24][O:23][C:22]1[CH:21]=[C:20]2[C:16]([C:17]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)(=[O:32])=[O:33])=[N:18][N:19]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:15][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58904782HCID 58904782, compound

Product 1

HCID 68853669HCID 68853669, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-(4-benzylpiperazin-1-yl)-6-methoxy-1-phenyl-3-(phenylsulfonyl)-1H-indazole (190 mg, 0.353 mmol) and 1-chloroethylchloroformate (250 mg, 1.77 mmol) in 1,2-dichloroethane is heated at reflux temperature for 4 h, cooled to room temperature and concentrated to dryness. The resultant residue is dissolved in ethanol, heated at reflux temperature for 16 h and concentrated in vacuo to give the title compound as a white solid, 130 mg, (82% yield). This compound is purified by recrystallization from ethanol/ether to afford a white solid, mp 167-170° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 h
  3. concentrationconcentrated to dryness
  4. dissolutionThe resultant residue is dissolved in ethanol
  5. temperatureheated
  6. temperatureat reflux temperature for 16 h
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f622e3a2ec494efe8be4e83e70edb269
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Reaction notes

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