Acetic Acid → Metosulam

HRID 619956

Reaction equation

HRID 619956 reaction equation
[Na].[CH3:2][OH:3].[Cl:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][S:14]([C:17]1[N:27]=[C:20]2[N:21]=[C:22](Cl)[CH:23]=[C:24](Cl)[N:19]2[N:18]=1)(=[O:16])=[O:15].[C:28]([OH:31])(=O)C>>[Cl:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][S:14]([C:17]1[N:27]=[C:20]2[N:21]=[C:22]([O:31][CH3:28])[CH:23]=[C:24]([O:3][CH3:2])[N:19]2[N:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 5360545SodiumHCID 150175485,7-Dichloro-N-(2,6-dichloro-3-methylphenyl)[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

Product 1

HCID 86422Metosulam

Procedure

Sodium (469 mg, 20.4 mmol) was added to 25 ml of methanol under nitrogen and allowed to react. The resulting solution was allowed to cool and then 2.14 g (5.0 mmol) of N-(2,6-dichloro-3-methylphenyl)-5,7-dichloro-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide were added with stirring. After about one hour, 1 ml of acetic acid was added and the mixture was poured into about 150 ml of ice water. The solid present was collected by filtration and dried to obtain 1.76 g (84.2 percent of theory) of the title compound as a white powder, m.p. 218°-221° C.

Workup

  1. customto react
  2. temperatureto cool
  3. filtrationThe solid present was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-3a815746826a401cbb191ee9205a2cc9
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Linked notes

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