HCID 178488009, compound → HCID 20428330, compound

HRID 615445Notes

Reaction equation

HRID 615445 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:22]=[CH:21][C:7]2[N:8]=[C:9]([NH:11][C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[NH:13])[S:10][C:6]=2[CH:5]=1>[OH-].[Na+].C(OCC)(=O)C>[CH3:2][O:3][C:4]1[CH:22]=[CH:21][C:7]2[N:8]3[C:9](=[N:8][C:7]4[CH:21]=[CH:22][CH:4]=[CH:5][CH:6]=4)[N:13]=[C:12]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:11]=[C:9]3[S:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 178488009HCID 178488009, compound

Product 1

HCID 20428330HCID 20428330, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the product from part (b) (2.0 g) in a mixture of sodium hydroxide solution (1N) and ethyl acetate (200 ml) was stirred until solution was obtained. The organic phase was removed, washed with water, dried and evaporated to a gum. A solution of the gum in dry dimethyl formamide (20 ml) was added to a stirred suspension of sodium hydride (300 mg of a 50% dispersion in oil) in the same solvent (20 ml) and stirring was continued for 1 h. A solution of phenylisothiocyanate (0.72 g) in dry dimethylformamide was added at room temperature and stirring continued for a further 2 h. Methyl iodide (0.7 g) was added and the reaction mixture allowed to stand at room temperature for 16 h. Addition of water (100 ml) resulted in the precipitation of a waxy solid which was collected and crystallised from acetonitrile to give the title compound as a pale cream crystals (400 mg), mp 213°-4°.

Workup

  1. customwas obtained
  2. customThe organic phase was removed
  3. washwashed with water
  4. customdried
  5. customevaporated to a gum
  6. additionA solution of the gum in dry dimethyl formamide (20 ml) was added to a stirred suspension of sodium hydride (300 mg of a 50% dispersion in oil) in the same solvent (20 ml)
  7. stirringstirring
  8. additionA solution of phenylisothiocyanate (0.72 g) in dry dimethylformamide was added at room temperature
  9. stirringstirring
  10. waitcontinued for a further 2 h
  11. additionMethyl iodide (0.7 g) was added
  12. waitto stand at room temperature for 16 h
  13. additionAddition of water (100 ml)
  14. customresulted in the precipitation of a waxy solid which
  15. customwas collected
  16. customcrystallised from acetonitrile

Sources & evidence

ORD record
ord-6f17c2d193414ecaaa346e72de66e135
Source dataset
uspto-grants-1985_02
Patent number
US04499269

Reaction notes

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