Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → HCID 19048089, compound

HRID 742622Notes

Reaction equation

HRID 742622 reaction equation
[OH:1][N:2]1[C:6]([O:7][CH3:8])=[N:5][NH:4][C:3]1=[O:9].[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[O:13]>C(#N)C>[OH:1][N:2]1[CH:6]([O:7][CH3:8])[N:5]([C:24]([NH:23][S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:12]([O:11][CH3:10])=[O:13])(=[O:22])=[O:21])=[O:25])[NH:4][C:3]1=[O:9]

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 15767501HCID 15767501, compound

Product 1

HCID 19048089HCID 19048089, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1.31 g (10 mmol) of 4-hydroxy-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.89 g (12 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate and 40 ml of acetonitrile is stirred for 5 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is stirred with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction and recrystallised from isopropanol. 1.22 g (33% of theory) of 4-hydroxy-5-methoxy-1-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 180° C. are obtained.

Workup

  1. concentrationsubsequently concentrated under a water pump vacuum
  2. stirringThe residue is stirred with diethyl ether
  3. customthe product which has been obtained in crystalline form
  4. customis isolated by filtration with suction
  5. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-1346b8f92d2c479d8b7a962d28b1de98
Source dataset
uspto-grants-1996_09
Patent number
US05554761

Reaction notes

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