Ethyl bromoacetate → 2-(2,4-Dimethoxyphenyl)-4H-1,3,4-thiadiazin-5(6H)-one

HRID 1380825Notes

Reaction equation

HRID 1380825 reaction equation
Br[CH2:2][C:3](OCC)=[O:4].[CH3:8][O:9][C:10]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[S:13].[OH-].[Na+]>>[CH3:8][O:9][C:10]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:11]=1[C:12]1[S:13][CH2:2][C:3](=[O:4])[NH:15][N:14]=1

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 13365894HCID 13365894, compound

Product 1

HCID 133659232-(2,4-Dimethoxyphenyl)-4H-1,3,4-thiadiazin-5(6H)-one

Conditions

Temperature
25 °C

Procedure

Ethyl bromoacetate (5.0 g.) was added to a stirred suspension of 2,4-dimethoxythiobenzohydrazide (6.5 g.) in aqueous 3N-sodium hydroxide solution (25 ml.) and the mixture was stirred at 25° C. for 18 hours and then filtered. The solid product was purified by flash chromatography on a silica gel column (Merck 9385) using a 30:1 v/v mixture of chloroform and methanol as eluant. The aqueous filtrate was acidified with aqueous 2N hydrochloric acid and the mixture was filtered. The solid products, both from the chromatographic purification and from the acidification, were combined and crystallised from aqueous methanol. There was thus obtained (2-(2,4-dimethoxyphenyl)-4H,6H-1,3,4-thiadiazin-5-one, m.p. 162°-164° C.

Workup

  1. filtrationfiltered
  2. customThe solid product was purified by flash chromatography on a silica gel column (Merck 9385)
  3. additiona 30:1 v/v mixture of chloroform and methanol as eluant
  4. filtrationthe mixture was filtered
  5. customThe solid products, both from the chromatographic purification
  6. customcrystallised from aqueous methanol

Sources & evidence

ORD record
ord-c730fa4b5cb84ff9a809f506c518cf8d
Source dataset
uspto-grants-1986_04
Patent number
US04584298

Reaction notes

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