HCID 10316709, compound → HCID 9997023, compound

HRID 1742095Notes

Reaction equation

HRID 1742095 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[C:8]([S:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(Cl)Cl.CC(O)C>O1CCCC1.Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]2[C:8]([S:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[N:7][N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 10316709HCID 10316709, compoundHCID 21906603Chloroform isopropyl alcohol

Product 1

HCID 9997023HCID 9997023, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.46 g (6.76 mmole) of 3 -n- butyl-5-(carbomethoxymethylthio)-4-(4-nitrobenzyl)-4H-1,2,4-triazole in 32 ml of tetrahydrofuran stirred in an ice bath was added gradually over 15 minutes a solution of 15.2 g (67.6 mmole) of stannous chloride dihydrate in 19 ml of concentrated HCl. The ice bath was removed, and the mixture was stirred at room temperature for 1.5 hours. It was then poured into a vigrously stirred mixture of 68 ml of 50% NaOH and 270 g. of ice. This was rapidly extracted with 3×300 ml of ether. The combined ether extracts were washed with 150 ml of H2O, then dried (MgSO4), filtered, and concentrated to give 566 mg (25%) of a white waxy solid, homogeneous by TLC in 97:3 CHCl3 -iPrOH; mass spectrum (FAB) m/e 335 (M+1)+. This material was used directly in the next reaction.

Workup

  1. customThe ice bath was removed
  2. additionIt was then poured into a vigrously stirred mixture of 68 ml of 50% NaOH and 270 g
  3. extractionThis was rapidly extracted with 3×300 ml of ether
  4. washThe combined ether extracts were washed with 150 ml of H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 566 mg (25%) of a white waxy solid
  9. customThis material was used directly in the next reaction

Sources & evidence

ORD record
ord-b8dba13dd0654060a576f34559ee429f
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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