Sodium Iodide → HCID 67336269, compound

HRID 1670551Notes

Reaction equation

HRID 1670551 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20]Cl)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[SH:30][C:31]1[NH:32][CH:33]=[CH:34][N:35]=1>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][S:30][C:31]3[NH:32][CH:33]=[CH:34][N:35]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 178527877HCID 178527877, compound

Product 1

HCID 67336269HCID 67336269, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (42.3 g, 128 mmol) in acetone (400 mL). Warm to 50° C., and then add potassium carbonate (26.5 g, 192 mmol) and sodium iodide (1.92 g, 12.8 mmol). With stirring, add 2-mercaptoimidazole (13.46 g, 134.4 mmol). Allow the mixture to stir at room temperature for 16 h. Filter the solid from this mixture, and wash the solid with acetone. Concentrate the filtrate in vacuo to a pink solid. Add DCM (400 mL) and 3% aqueous NaHCO3 (400 mL). Collect the organic layer, and back extract the aqueous with DCM (2×100 mL). Combine the organic extracts and wash successively with brine (2×100 mL) and saturated aqueous NaHCO3 (1×50 mL). Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain 3-tert-butoxycarbonyl-7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an off-white solid (46.3 g, 92%). MS (ES+) m/z: 394.3 (M+H)+.

Workup

  1. stirringAllow the mixture to stir at room temperature for 16 h
  2. filtrationFilter the solid from this mixture
  3. washwash the solid with acetone
  4. concentrationConcentrate the filtrate in vacuo to a pink solid
  5. customCollect the organic layer
  6. extractionback extract the aqueous with DCM (2×100 mL)
  7. washCombine the organic extracts and wash successively with brine (2×100 mL) and saturated aqueous NaHCO3 (1×50 mL)
  8. dry with materialDry the organic layer over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-af76d4eddc6e4ccc9435e6ea77d5c18b
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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