Acetic Acid → 2-[[(1-Ethyl-5-methylthio-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester

HRID 904988Notes

Reaction equation

HRID 904988 reaction equation
[CH3:1][S:2][C:3]1[NH:7][N:6]=[C:5]([NH:8][C:9]([NH:11][S:12]([C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[O:10])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](I)[CH3:32].C(O)(=O)C>CC(C)=O.C(#N)C>[CH2:31]([N:7]1[C:3]([S:2][CH3:1])=[N:4][C:5]([NH:8][C:9]([NH:11][S:12]([C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[O:10])=[N:6]1)[CH3:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178497660HCID 178497660, compound

Product 1

HCID 132453552-[[(1-Ethyl-5-methylthio-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 1.0 gram (0.0027 mole) of methyl 2-[(5-methylthio-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonylbenzoate and 0.7 grams of potassium carbonate in 30 ml of acetone at room temperature, 0.8 ml of ethyl iodine was added by way of syringe and the resulting white suspension stirred 3 days. The mixture was poured into 250 ml of ice water and acidified to pH 3-4 with glacial acetic acid. The aqueous acidic mixture was extracted with 1:1 mixture of ethyl ether/ethyl acetate and the extract washed with brine, dried (MgSO4), and evaporated to yield a white solid residue which was suspended in acetonitrile and filtered, yield 0.3 grams, m.p. 188°-191°.

Workup

  1. extractionThe aqueous acidic mixture was extracted with 1:1 mixture of ethyl ether/ethyl acetate
  2. washthe extract washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto yield a white solid residue which
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0feed14454cc43edbc49b5a594be27c9
Source dataset
uspto-grants-1983_12
Patent number
US04421550

Reaction notes

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