Water → HCID 23225432, compound

HRID 741688Notes

Reaction equation

HRID 741688 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH:12](Br)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[SH:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.[OH-].[Na+].O>CCO>[C:13]1([C:12]2[S:21][C:22]3=[N:26][CH:25]=[CH:24][N:23]3[C:11]=2[C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 19426789HCID 19426789, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 23225432HCID 23225432, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the bromoketone of step 2 of example 8 (141.2 mg, 4 mmol), 2-mercaptoimidazole (400 mg, 4 mmol) and NaOH (400 μL, 10 N) in EtOH (4 mL) was stirred at r.t. for 6 h. H2O was added and the precipitate that formed was filtered. The solid was washed with water and dried under vaccum. The dried solid residue (234 mg) was heated with P2O5 (900 mg) in PPA (3.5 mL) at 170 ° C. for 20 h. The mixture was quenched with ice and NH4OAc and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to a solid. The solid residue was chromatographed on silica gel (eluted with 40 % EtOAc/Hexane) to give 113 mg of the title compound. 1H NMR (CD3COCD3): δ3.10 (s, 3H), 7.40-7.20 (m, 7H), 7.65 (d, 2H), 8.00 (d, 2H).

Workup

  1. customthe precipitate that formed
  2. filtrationwas filtered
  3. washThe solid was washed with water
  4. customdried under vaccum
  5. temperatureThe dried solid residue (234 mg) was heated with P2O5 (900 mg) in PPA (3.5 mL) at 170 ° C. for 20 h
  6. customThe mixture was quenched with ice and NH4OAc
  7. extractionextracted with EtOAc
  8. washThe organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to a solid
  12. customThe solid residue was chromatographed on silica gel (eluted with 40 % EtOAc/Hexane)

Sources & evidence

ORD record
ord-cf004583987e419cb8c69de0ee8c2262
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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