Triethylamine → 2-[2-(Methylthio)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-one

HRID 499552Notes

Reaction equation

HRID 499552 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[CH:5][CH:4]=1)#[N:2].[C:11](OC)(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[SH:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:10][S:9][C:7]1[N:6]=[CH:5][CH:4]=[C:3]([C:1]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[C:11](=[O:19])[N:2]=2)[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 2957772-(Methylthio)-4-pyrimidinecarbonitrile

Product 1

HCID 597502412-[2-(Methylthio)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-oneYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Cyano-2-methylthiopyrimidine (1.37 g, 9.06 mmol) and methyl thiosalicylate (3.05 g, 18.1 mmol) were dissolved in toluene (30 ml), and triethylamine (3.80 ml, 27.2 mmol) was added thereto. The mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was recrystallized from ethanol to give the titled compound (1.40 g, 54%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4a6f988b1f1c4ddbb22fe831199d23ac
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…