Hydrochloric Acid → HCID 57590531, compound

HRID 1783489Notes

Reaction equation

HRID 1783489 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl.[OH-].[Na+]>CCO.CO.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 57590537HCID 57590537, compound

Product 1

HCID 57590531HCID 57590531, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-nitrobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester, from Example 7 (35.7 mmol theory), SnCl2 (40.25 g, 178.4 mmol), and concentrated HCl solution (4.46 mL) in EtOH was heated at 70° C. overnight, cooled, diluted with 20% MeOH in CH2Cl2, neutralized with NaOH to pH 8-10 and extracted with CHCl3. The extracts were combined, dried over Na2SO4, concentrated, and purified by chromatography with 1-5% MeOH in CH2Cl2 to provide the title compound (3.0 g, 24% overall yield from 4-nitro-3H-benzoxazole-2-thione), characterized by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. extractionextracted with CHCl3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by chromatography with 1-5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-fba89f3bd59b43ef9b44ba6c7ff64902
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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