Ammonium Hydroxide → HCID 10229209, compound

HRID 860815Notes

Reaction equation

HRID 860815 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:13]2[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=2)=[CH:8][C:7]=1[CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=1)[S:27][CH2:28][CH2:29][C:30](O)=[O:31].[NH4+].[OH-]>C1COCC1>[Cl:39][C:35]1[CH:34]=[C:33]([CH:26]2[C:7]3[CH:8]=[C:9]([CH:12]([C:19]4[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=4)[C:13]4[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=4)[CH:10]=[CH:11][C:6]=3[NH:5][C:30](=[O:31])[CH2:29][CH2:28][S:27]2)[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 69021738HCID 69021738, compound

Product 1

HCID 10229209HCID 10229209, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (1 ml) was added slowly to a mixture of intermediate (22) (0.00456 mol) in THF (15 ml). The mixture was stirred and refluxed for 2.5 hours, poured out on ice and NH4OH and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 20–45 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN and diethyl ether. The precipitate was filtered off and dried in vacuo. The residue was recrystallized from CH3CN and diethyl ether. The precipitate was filtered off and dried in vacuo, yielding 0.08 g (3%) of 6-(3-chlorophenyl)-8-[(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-1,3,4,6-tetrahydro-2H-5,1-benzothiazocin-2-one, mp. 199° C.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness
  7. customThe residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 20–45 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from CH3CN and diethyl ether
  11. filtrationThe precipitate was filtered off
  12. customdried in vacuo
  13. customThe residue was recrystallized from CH3CN and diethyl ether
  14. filtrationThe precipitate was filtered off
  15. customdried in vacuo

Sources & evidence

ORD record
ord-b13040f7244c46bcbfdf999a3b17a624
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

Loading…