Sodium Thiosulfate → HCID 59556567, compound

HRID 1172957Notes

Reaction equation

HRID 1172957 reaction equation
[CH3:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:10][C:5]2=[N:4][CH:3]=1.C1C(=O)N([I:28])C(=O)C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl>[CH2:14]([O:13][C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([CH3:1])=[C:3]([I:28])[N:4]=[C:5]2[CH2:10]1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 59556588HCID 59556588, compound

Product 1

HCID 59556567HCID 59556567, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of benzyl 3-methyl-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (1.085 g, 4.00 mmol) in 1,2-dichloroethane (60 ml) was added NIS (4.50 g, 20.00 mmol) and the reaction was heated at reflux for one hour. The reaction was cooled to room temperature and poured into 100 ml of saturated 5% sodium thiosulfate solution. The layers were separated and the aqueous layer was re-extracted with 1,2-dichloroethane (40 ml). The combined organic layers were washed with water (100 ml), dried over sodium sulfate, filtered and concentrated. Product was extracted from the residue by trituration with 3×50 ml portions of ether. The extract was filtered and concentrated to yield 2-Iodo-3-methyl-5,6-dihydro-8H-imidazo[1,2-a] pyrazine-7-carboxylic acid benzyl ester (1.42 g, 89%) as a pale yellow oil. LCMS (Table 1, Method a) Rt=3.32 min, m/z 398.59 (M+H)+; 1H NMR (400 MHz, CHCl3)δ 7.35 (m, 5H), 5.13 (s, 2H), 4.56 (s,broad, 2H), 4.38 (t, 2H), 3.82 (s, broad, 2H), 2.09 (s, 3H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for one hour
  3. customThe layers were separated
  4. extractionthe aqueous layer was re-extracted with 1,2-dichloroethane (40 ml)
  5. washThe combined organic layers were washed with water (100 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. extractionProduct was extracted from the residue by trituration with 3×50 ml portions of ether
  10. filtrationThe extract was filtered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ccff740f69f5499eb13de4ee65c00860
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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