1-Chloroethyl chloroformate → HCID 22174822, compound

HRID 225431Notes

Reaction equation

HRID 225431 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([N:19]4[CH2:24][CH2:23][N:22](CC5C=CC=CC=5)[CH2:21][CH2:20]4)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:32]C(OC(Cl)C)=O>ClCCCl>[ClH:32].[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22174832HCID 22174832, compound

Product 1

HCID 22174822HCID 22174822, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-phenylsulfonyl-4-(4-benzylpiperazin-1-yl)-1H-indazole (433 mg, 1.0 mmol) in 1,2-dichloroethane is treated with 1-chloroethyl chloroformate (0.27 mL, 2.5 mmol) heated at reflux temperature for 2 hr, and concentrated in vacuo. The resultant residue is heated at reflux temperature in methanol for 1.5 hr, cooled, concentrated in vacuo and reconcentrated from ether. The resulting tan solid is triturated with ether and crystallized from hot ethanol to give the title compound as a tan solid 237 mg (63% yield), mp 203-205° C., identified by HNMR and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hr
  3. concentrationconcentrated in vacuo
  4. temperatureThe resultant residue is heated
  5. temperatureat reflux temperature in methanol for 1.5 hr
  6. temperaturecooled
  7. concentrationconcentrated in vacuo
  8. customThe resulting tan solid is triturated with ether
  9. customcrystallized from hot ethanol

Sources & evidence

ORD record
ord-96f30fcf50fb466ab4758d9d39b63986
Source dataset
uspto-grants-2009_07
Patent number
US07557098B2

Reaction notes

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