2,4-Dihydro-5-methoxy-4-methyl-3H-1,2,4-triazol-3-one → Thiencarbazone-methyl

HRID 2243448Notes

Reaction equation

HRID 2243448 reaction equation
[CH3:1][O:2][C:3]1[N:4]([CH3:9])[C:5](=[O:8])[NH:6][N:7]=1.[N:10]([S:13]([C:16]1[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][S:19][C:20]=1[CH3:21])(=[O:15])=[O:14])=[C:11]=[O:12]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]([CH3:9])[C:5](=[O:8])[N:6]([C:11]([NH:10][S:13]([C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][S:19][C:20]=2[CH3:21])(=[O:14])=[O:15])=[O:12])[N:7]=1

Participants

4

Reactant 2

HCID 108771452,4-Dihydro-5-methoxy-4-methyl-3H-1,2,4-triazol-3-oneHCID 579578313-Thiophenecarboxylic acid, 4-(isocyanatosulfonyl)-5-methyl-, methyl ester

Product 1

HCID 11205153Thiencarbazone-methylYield 93.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
70 °C

Procedure

12.9 g of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (3) (100 mmol) were initially charged in 200 ml of xylene and heated to 70° C. At this temperature, 119 g of a 22% solution of methyl 4-(isocyanatosulfonyl)-5-methylthiophene-3-carboxylate (2) (100 mmol) in dry xylene were metered in. The mixture was stirred at 70° C. for a further 5.8 h. Subsequently, workup was effected at room temperature by filtering the precipitated product. After washing with 50 ml of xylene and subsequently drying, 36.4 g of methyl 4-({[(3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]amino}-sulfonyl)-5-methylthiophene-3-carboxylate (4) (91% of theory, content relative to standard: 97.5%) of melting point 201° C. were obtained.

Workup

  1. customwas effected at room temperature
  2. filtrationby filtering the precipitated product
  3. washAfter washing with 50 ml of xylene
  4. customsubsequently drying

Sources & evidence

ORD record
ord-d94f0249900f4f31b6326961710bc44e
Source dataset
uspto-grants-2010_03
Patent number
US07674917B2

Reaction notes

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