Sodium Iodide → HCID 178456408, compound

HRID 2296613Notes

Reaction equation

HRID 2296613 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[NH:14])=[CH:11][C:6]=2[CH2:5][NH:4][CH2:3][CH2:2]1.[C:20](=[O:23])([O-:22])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH3:29].[I-].[Na+].CN(C=[O:36])C>>[C:7]([OH:36])(=[O:1])/[CH:6]=[CH:11]/[C:20]([OH:22])=[O:23].[CH2:27]([N:4]1[CH2:5][C:6]2[CH:11]=[C:10]([NH:12][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[NH:14])[CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3]1)[CH2:28][CH3:29].[CH2:27]([N:4]1[CH2:5][C:6]2[CH:11]=[C:10]([NH:12][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[NH:14])[CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3]1)[CH2:28][CH3:29]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 178511887HCID 178511887, compound

Product 1

HCID 178456408HCID 178456408, compound

Procedure

To N-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-2-thiophenecarboximidamide (1.57 g, 6 mmol) in DMF (75 ml) was added potassium carbonate (9 g) and 1-bromopropane (1.48 g, 12 mmol) and a catalytic amount of sodium iodide. The mixture was stirred for 48 h and was then filtered. The solids were dissolved in water (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were dried with magnesium sulfate, filtered and concentrated to a solid. The solids were recrystallized from hot isopropanol. The solids were dissolved in ethyl acetate, treated with isopropanol-fumaric acid, and triturated with ether. The hemifumarate salt was collected by filtration (0.86 g, 39%), m.p. 174° C.

Workup

  1. filtrationwas then filtered
  2. dissolutionThe solids were dissolved in water (50 ml)
  3. extractionextracted with methylene chloride (3×50 ml)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. customThe solids were recrystallized from hot isopropanol
  8. dissolutionThe solids were dissolved in ethyl acetate
  9. additiontreated with isopropanol-fumaric acid
  10. customtriturated with ether
  11. filtrationThe hemifumarate salt was collected by filtration (0.86 g, 39%), m.p. 174° C.

Sources & evidence

ORD record
ord-2e5acba7e0854fc5b47942341a2bd57a
Source dataset
uspto-grants-2002_12
Patent number
US06489322B1

Reaction notes

Loading…