Hydrochloric Acid → HCID 21935303, compound

HRID 1241541Notes

Reaction equation

HRID 1241541 reaction equation
Cl[CH2:2][C:3]1[C:4]([O:12][C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)=[C:5]([I:11])[C:6](=[O:10])[NH:7][C:8]=1[CH3:9].NC(N)=[S:23].[OH-].[Na+].Cl>CS(C)=O>[CH3:20][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([CH3:19])[CH:16]=1)[O:12][C:4]1[C:3]([CH2:2][SH:23])=[C:8]([CH3:9])[NH:7][C:6](=[O:10])[C:5]=1[I:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 21935285HCID 21935285, compound

Product 1

HCID 21935303HCID 21935303, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of compound 125 (1.5 g; 0.0037 mol) and thiourea (0.31 g; 0.00408 mol) in DMSO (30 ml) was stirred at room temperature for 1 hour. NaOH 3N was added. The mixture was stirred for 15 minutes, acidified with HCl 3N and extracted with ethylacetate (EtOAc). The organic layer was separated, dried on magnesium sulfate (MgSO4), filtered and the solvent was evaporated. The residue was taken up in DIPE and filtered. The precipitate (1.2 g) was purified by column chromatography over silica gel (eluent: EtOAc 100%; 35–70 μm) and dried to yield 0.3 g (20%).

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. extractionextracted with ethylacetate (EtOAc)
  3. customThe organic layer was separated
  4. customdried on magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. filtrationfiltered
  8. customThe precipitate (1.2 g) was purified by column chromatography over silica gel (eluent: EtOAc 100%; 35–70 μm)
  9. customdried
  10. customto yield 0.3 g (20%)

Sources & evidence

ORD record
ord-b78b98ce6b454b60b90e0568afb706e2
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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