HCID 178458742, compound → HCID 178458741, compound

HRID 2106790Notes

Reaction equation

HRID 2106790 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:6]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[CH:19]=[CH:18][C:7]=2[S:8][C:9]=1[C:10]([NH:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1)=[O:11])[CH3:3]>[Pd].C(O)(=O)C>[CH3:3][CH:2]([O:4][C:5]1[C:6]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:7]=2[S:8][C:9]=1[C:10]([NH:12][C:13]1[NH:14][N:15]=[N:16][N:17]=1)=[O:11])[CH3:1]

Participants

4

Reactant 1

HCID 178458742HCID 178458742, compound

Product 1

HCID 178458741HCID 178458741, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A warm slurry of 3-(1-methylethoxy)-5-(phenylmethoxy)-N-1H-tetrazol-5-yl-benzo[b]thiophene-2carboxamide (1.9 g, 5 mmoles) and 20% palladium on carbon (0.5 g) in acetic acid (250 mls) is shaken under hydrogen (50 psig) in a Parr apparatus. After three hours additional catalyst (0.5 g) is added and the mixture shaken at ambient temperature for 15 hours. The catalyst is removed by filtration and rinsed with warm acetic acid (200 mls). The filtrate is stripped of solvent under reduced pressure and two portions (50 mls) of toluene are added to, then stripped from the residue, leaving the crystalline product. Recrystallization from methanol gave the pure 3-(1-methylethoxy)-5-hydroxy -N-1H-tetrazol-5-yl-benzo[b]thiophene-2-carboxamide (0.7 g): mp=258° C. (dec).

Workup

  1. customThe catalyst is removed by filtration
  2. washrinsed with warm acetic acid (200 mls)
  3. additionare added to,
  4. customleaving the crystalline product
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-4892769042454b5db96abd546c436dfb
Source dataset
uspto-grants-1990_06
Patent number
US04931459

Reaction notes

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