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

HRID 748370Notes

Reaction equation

HRID 748370 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-059439cbba064f9a9a055905c8a79006
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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