Methanol → 2-Acetylamino-8-methoxy-4-phenylimino-4H-1,3,5-triazino[2,1-b]benzothiazole

HRID 615443Notes

Reaction equation

HRID 615443 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[N:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=1)[C:7]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:6]=1[S:5]2.[C:24](OC(=O)C)(=[O:26])[CH3:25].CO>N1C=CC=CC=1>[C:24]([NH:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[N:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=1)[C:7]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:6]=1[S:5]2)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 204283092-Amino-8-methoxy-4-phenylimino-4H-1,3,5-triazino[2,1-b]benzothiazole

Product 1

HCID 1357975462-Acetylamino-8-methoxy-4-phenylimino-4H-1,3,5-triazino[2,1-b]benzothiazoleYield 79.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-8-methoxy-4-phenylimino-4H-1,3,5-triazino[2,1-b]benzothiazole (0.3 g) and acetic anhydride (0.14 g) in dry pyridine (15 mls) were heated at 100° for 24 hours. After cooling to room temperature, methanol (5 mls) was added, the solution was stirred for 1 hour and the solvents were removed in vacuo. The residue was dissolved in chloroform, the solution washed with water, brine, dried (Na2SO4) and evaporated in vacuo to give a yellow solid (0.27 g). Purification by chromatography (silica gel, chloroform) gave the title compound as pale yellow crystals (0.18 g), mp 248°-29°.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washthe solution washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4c398afa0cc54205829a80cbce2b62ff
Source dataset
uspto-grants-1985_02
Patent number
US04499269

Reaction notes

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