Methyl iodide → 2-Amino-4-[4-(2-diethylaminoethoxy)phenyl]imino-8-methoxy-4H-1,3,5-triazino[2,1-b]benzothiazole

HRID 615444Notes

Reaction equation

HRID 615444 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH2:13])=[NH:12])[S:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH2:18]([N:20]([CH2:33][CH3:34])[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=S)=[CH:26][CH:25]=1)[CH3:19].CI>CN(C)C=O.O>[NH2:12][C:11]1[N:10]=[C:8]2[N:7]([C:31](=[N:30][C:27]3[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][N:20]([CH2:18][CH3:19])[CH2:33][CH3:34])=[CH:29][CH:28]=3)[N:13]=1)[C:6]1[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[S:9]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 226409854-(2-Diethylaminoethoxy)phenylisothiocyanateHCID 178488010N-(6-methoxy-1,3-benzothiazol-2-yl)guanidine

Product 1

HCID 204283262-Amino-4-[4-(2-diethylaminoethoxy)phenyl]imino-8-methoxy-4H-1,3,5-triazino[2,1-b]benzothiazoleYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Methoxybenzothiazol-2-ylguanidine (0.2 g) was added to a suspension of sodium hydride (0.022 g=0.044 g of 50% dispersion in oil) in anhydrous dimethylformamide (20 mls) and the resulting mixture was stirred at room temperature for 15 mins. 4-(2-Diethylaminoethoxy)phenylisothiocyanate (0.23 g) was added followed, after 2.5 hrs, by methyl iodide (0.14 g) and the mixture stirred for a further 18 hrs. Water was added to precipitate a yellow solid which was collected by filtration, washed with ethanol and dissolved in ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulphate and evaporated to give a yellow solid (0.33 g). Recrystallisation of the residue from ethyl acetate gave the desired product as pale yellow crystals (0.08 g) mp 189.5°-191°.

Workup

  1. stirringthe mixture stirred for a further 18 hrs
  2. customto precipitate a yellow solid which
  3. filtrationwas collected by filtration
  4. washwashed with ethanol
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-8bbac0580d6147beb3d43304b3ffdf7f
Source dataset
uspto-grants-1985_02
Patent number
US04499269

Reaction notes

Loading…