Thionyl Chloride → HCID 15294730, compound

HRID 1190794Notes

Reaction equation

HRID 1190794 reaction equation
Cl.C([NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][N:16]3[CH:20]=[N:21][CH:22]=[C:15]23)=[CH:10][CH:9]=1)(C)(C)C.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH:22]1[N:21]=[CH:20][N:16]2[CH2:17][CH2:18][CH2:19][CH:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]#[N:6])=[CH:13][CH:12]=3)[C:15]=12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69292992HCID 69292992, compound

Product 1

HCID 15294730HCID 15294730, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.74 mmol of N-tert-Butyl-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-yl)-benzamide hydrochloride and 1.4 ml of thionyl chloride in 30 ml of chloroform is stirred under reflux for 7 hours. The reaction mixture is cooled to room temperature and evaporated. The residue is taken up in dichloromethane and mixed with saturated aqueous sodium bicarbonate solution. The organic phase is separated off and the aqueous phase is extracted with dichloromethane (2×). The combined organic phases are dried with sodium sulphate and evaporated. Following flash chromatography (SiO2 60F) of the residue, the resulting solid is stirred in 1:1 diethyl ether/tert-butyl methyl ether, filtered and dried. The title compound is obtained as a cream-colored solid. Rf=0.37 (toluene:methanol=85:15); Rt=4.88

Workup

  1. temperatureunder reflux for 7 hours
  2. customevaporated
  3. additionmixed with saturated aqueous sodium bicarbonate solution
  4. customThe organic phase is separated off
  5. extractionthe aqueous phase is extracted with dichloromethane (2×)
  6. dry with materialThe combined organic phases are dried with sodium sulphate
  7. customevaporated
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-28e2c927390348018e35798d50e42ba6
Source dataset
uspto-grants-2014_03
Patent number
US08680079B2

Reaction notes

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