5-benzyl-1,3,5-triazinane-2-thione → HCID 13059232, compound

HRID 543881Notes

Reaction equation

HRID 543881 reaction equation
Br[CH:2]([C:7](=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH2:18]([N:25]1[CH2:30][NH:29][C:28](=[S:31])[NH:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH2:18]([N:25]1[CH2:30][N:29]2[C:7]([OH:17])([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=3)[CH:2]([CH2:3][C:4]([OH:6])=[O:5])[S:31][C:28]2=[N:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6748065-benzyl-1,3,5-triazinane-2-thioneHCID 20461135HCID 20461135, compound

Product 1

HCID 13059232HCID 13059232, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-bromo-3-(m-nitrobenzoyl)propionic acid (3.78 g, 0.0125 mole) in methanol (50 ml) was mixed with a suspension of 5-benzyl-3,4,5,6-tetrahydro-s-triazin-2(1H)thione (2.6 g, 0.0125 mole) in the same solvent (150 ml). The mixture was warmed until a clear solution was obtained and allowed to stand for two hours. Evaporation of the solvent gave a yellow solid foam (5.3 g, 83%). 2.5 Grams of this material were dissolved in warm ethanol and a colourless solid gradually crystallised and was collected to give 3-benzyl-7-carboxymethyl-6-hydroxy-6-(m-nitrophenyl)-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazine hydrobromide (1.2 g), m.p. 147°-148° C. (decomposition).

Workup

  1. temperatureThe mixture was warmed until a clear solution
  2. customwas obtained
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-452765c8caf24e35aef406d7c2ffac82
Source dataset
uspto-grants-1984_05
Patent number
US04447604

Reaction notes

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