Hydrochloric Acid → 5-Methyl-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),5-trien-3-one

HRID 1875500

Reaction equation

HRID 1875500 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7]([O:9]CC)=O.Cl.[CH3:17][C:18]#[N:19]>>[CH3:17][C:18]1[NH:19][C:7](=[O:9])[C:6]2[C:5]3[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Product 1

HCID 2093955-Methyl-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),5-trien-3-oneYield 62%

Procedure

To a 25 ml flask was added 4 (225 mg, 1 mmol) and 10 ml CH3CN. HCl gas was passed through the solution for 3 h, before the solvent was evaporated under reduced pressure. The residue was dissolved in 10 mL distilled water and treated with ammonia water solution to generate a white precipitate. The precipitate was collected by filtration to afford 143 mg (62%) of 5 as a white solid: 1H NMR (DMSO-d6) δ 1.75 (m, 4H), 2.48 (s, 3H), 2.69 (m, 2H), 2.83 (m, 2H), 12.16 (s, 1H). Anal. (C11H12N2OS) m/z (ESI) 220.067811 [M]+.

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 10 mL
  3. distillationdistilled water
  4. additiontreated with ammonia water solution
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-db84033599ff4cc78a99e4a8e64afebe
Source dataset
uspto-grants-2012_11
Patent number
US08309564B2

Linked notes

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