Benzoic Acid → HCID 178527217, compound

HRID 906035Notes

Reaction equation

HRID 906035 reaction equation
[S:1]([Cl:4])([Cl:3])=[O:2].[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.C(O)(=O)C1C=CC=CC=1>C(Cl)Cl>[O:2]=[S:1]([Cl:4])[Cl:3].[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 24386Thionyl ChlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 178527217HCID 178527217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A stock solution of SOCl2-benzotriazole in dry DCM (1.5 M) was prepared by making up volume of a viscous clear solution of thionyl chloride (1 eq) and benzotriazole (1 eq) with dry DCM (1.5 M)—cf, Synlett 1999, 1763. 1.25 eq of this stock solution was added to a solution of 4-(4-tert-butoxycarbonyl)piperazin-1-yl)benzoic acid (1 eq) (prepared as described in published International patent application WO98/00134) in dry DCM (0.05 M). With the addition, a precipitate formed that was indicative of acyl chloride formation. The reaction was left at RT for 10 min before being filtered through a pad of anhydrous sodium sulfate.

Workup

  1. additionWith the addition
  2. customa precipitate formed
  3. filtrationbefore being filtered through a pad of anhydrous sodium sulfate

Sources & evidence

ORD record
ord-62976d579ded4e69ba81f0e5317dcb6a
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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