1-Chloroethyl chloroformate → HCID 9859629, compound

HRID 356115Notes

Reaction equation

HRID 356115 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[S:14][C:15]3[CH2:24][C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:16]=3[N:17]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[S:14][C:15]3[CH2:24][C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:16]=3[N:17]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18940990HCID 18940990, compound

Product 1

HCID 9859629HCID 9859629, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.86 g of 2-(1-benzyl-3-pyrrolidinyl)-8H-indeno[1,2-d]thiazole in 5 ml of dichloroethane was added 5 ml of 1-chloroethyl chloroformate, followed by heating under reflux for 2 hours. After cooling, the solvent was evaporated and 10 ml of methanol was added to the resulting residue, followed by heating under reflux for 2 hours. After the completion of the reaction, ethyl acetate was added to the reaction mixture, followed by extraction with 1N hydrochloric acid. The extract was neutralized with sodium bicarbonate, followed by the extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated, whereby 0.18 g of 2-(3-pyrrolidinyl)-8H-indeno[1,2-d]thiazole was obtained. The resulting product was dissolved in methanol. Fumaric acid was added to the resulting solution to cause crystallization, and the crystals were recrystallized from acetonitrile-methanol to obtain a fumarate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. addition10 ml of methanol was added to the resulting residue
  6. temperatureby heating
  7. temperatureunder reflux for 2 hours
  8. customAfter the completion of the reaction, ethyl acetate
  9. additionwas added to the reaction mixture
  10. extractionfollowed by extraction with 1N hydrochloric acid
  11. extractionfollowed by the extraction with chloroform
  12. dry with materialThe extract was dried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-26b2fbb406674531bda0d9a50d57f9cd
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

Loading…