1-Chloroethyl chloroformate → HCID 58817577, compound

HRID 1986931Notes

Reaction equation

HRID 1986931 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:22][CH:21]=[CH:20][C:16]=3[N:17]([CH3:19])[N:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>C(Cl)Cl>[CH3:19][N:17]1[C:16]2[CH:20]=[CH:21][S:22][C:15]=2[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:18]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18436986HCID 18436986, compound

Product 1

HCID 58817577HCID 58817577, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a mixture of 3-(4-Benzyl-piperazin-1-yl)-1-methyl-1H-thieno[3,2-c]pyrazole and the 2-methyl analog (189.0 g, 0.60 mol) is dissolved in DCM (1.25 L) is added 1-chloroethylchloroformate (78.6 mL, 0.72 mol). The solution is heated at reflux for 1 hour when the mixture is cooled and the solvent is removed by evaporation. The residue is taken up in methanol (1 L) and heated at reflux for 30 minutes. After cooling, the solution is treated with 1 N HCl in ether (200 mL) and an additional 1 L of ether to afford the precipitation of the product. The solid is collected via filtration and washed with cold ether. The solid is recrystallized from methanol (1 L) and the HCl salt is collected by filtration, washed with ether and dried under vacuum yielding 123.04 g (80%) of the desired product as an 80:1 mixture of regioisomers in favor of the desired regioisomer as seen by NMR.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour when the mixture
  3. temperatureis cooled
  4. customthe solvent is removed by evaporation
  5. temperatureheated
  6. temperatureat reflux for 30 minutes
  7. temperatureAfter cooling
  8. additionthe solution is treated with 1 N HCl in ether (200 mL)
  9. customan additional 1 L of ether to afford
  10. customthe precipitation of the product
  11. filtrationThe solid is collected via filtration
  12. washwashed with cold ether
  13. customThe solid is recrystallized from methanol (1 L)
  14. filtrationthe HCl salt is collected by filtration
  15. washwashed with ether
  16. customdried under vacuum

Sources & evidence

ORD record
ord-f4532388306b4afb91c6009675422478
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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