Hydrochloric Acid → HCID 19102794, compound

HRID 1198677Notes

Reaction equation

HRID 1198677 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28][N:27]([C:34]3[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[CH:36][C:35]=3[C:43]([F:46])([F:45])[F:44])[C:26]2=[O:47])=[CH:20][CH:19]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C1COCC1>[NH2:40][C:37]1[CH:38]=[CH:39][C:34]([N:27]2[C:26](=[O:47])[N:25]([CH2:24][C:21]3[CH:20]=[CH:19][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:9](=[O:10])(=[O:11])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[CH:23][CH:22]=3)[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28]2)=[C:35]([C:43]([F:44])([F:45])[F:46])[CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19102789Carbamic acid, [[4′-[[3-butyl-1,5-dihydro-1-[4-nitro-2-(trifluoromethyl)phenyl]-5-oxo-4H-1,2,4-triazol-4-yl]methyl][1,1′-biphenyl]-2-yl]sulfonyl]-, 1,1-dimethylethyl ester

Product 1

HCID 19102794HCID 19102794, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared from 4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 21) by treatment with excess stannous chloride and concentrated hydrochloric acid in THF at 0° C. The reaction is worked up by treatment with excess sodium hydroxide, and the product is extracted with ethyl acetate. After drying over anhydrous sodium sulfate and removal of volatiles, the crude product is flash chromatographed over silica gel to afford the desired material.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. dry with materialAfter drying over anhydrous sodium sulfate and removal of volatiles
  3. customchromatographed over silica gel

Sources & evidence

ORD record
ord-2094a83ce54243fcb638d8c7898fe0e2
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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