Acetonitrile → HCID 18936844, compound

HRID 357164Notes

Reaction equation

HRID 357164 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:26](=[O:27])[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:18]4[S:19](=[O:24])(=[O:23])[CH2:20][CH2:21][CH2:22][N:17]4[C:16]3=[O:34])=[CH:8][CH:7]=[CH:6][C:5]=12.[I-].C[CH:37]=[N+:38]=[CH:39]C.[C:41](#N)C>>[CH3:37][N:38]([CH2:39][C:3]1[N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:26](=[O:27])[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:18]4[S:19](=[O:24])(=[O:23])[CH2:20][CH2:21][CH2:22][N:17]4[C:16]3=[O:34])=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1)[CH3:41]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 18936633HCID 18936633, compoundHCID 21892197N,N-dimethylmethyleneammoniumiodide

Product 1

HCID 18936844HCID 18936844, compound

Procedure

To a solution of 0.45 g (0.93 mmol) of 7-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]-1,1-dioxo-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione in 10 ml of acetonitrile, 0.258 g (1.4 mmol) of N,N-dimethylmethylene ammonium iodide (Eschenmoser's salt) was added at room temperature, followed by refluxing for 2 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=25/1) to yield 0.40 g (77.6%, light yellow oily substance) of the desired product.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-511967080fc54647bf7b22b26ef23da9
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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