Hydrochloric Acid → HCID 178439171, compound

HRID 2082377Notes

Reaction equation

HRID 2082377 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]([CH:46]=[O:47])=[CH:6][CH:5]=1)[CH2:2][CH3:3].Cl>C1COCC1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[C:7]([CH:46]=[O:47])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14987391HCID 14987391, compound

Product 1

HCID 178439171HCID 178439171, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-n-propyl-1-[2'-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl-methyl]pyrrole-2-carboxaldehyde (4.05 g, 6.6 mmol) in THF (25 ml) was added 4N HCl (11 ml) with stirring. The mixture was stirred at room temperature for 5 hours. The THF was removed by rotary evaporation and the residue was adjusted to pH 5-6 with 4N NOH (~10 ml). The product was extracted into EtOAc (2×50 ml), the organic layer was dried (MgSO4), filtered and concentrated. Flash chromatography of the reddish solid residue (1.97 g) on silica gel (30 g; EtOAc/hexanes, 1/1) gave 1.4 g of the title compound as a pale pink solid; m.p. 68°-71° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. customThe THF was removed by rotary evaporation
  3. extractionThe product was extracted into EtOAc (2×50 ml)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-061bd031d6154848b23f16067aa16ab5
Source dataset
uspto-grants-1993_02
Patent number
US05189048

Reaction notes

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