Hydrochloric Acid → HCID 53740933, compound

HRID 864963Notes

Reaction equation

HRID 864963 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].CC(C)([O-])C.[K+].Cl[CH:24]([CH3:27])[C:25]#[N:26].Cl>CS(C)=O.C(OCC)(=O)C>[CH3:10][O:9][C:7]([C:6]1[S:5][C:4]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:3]=2[C:2]=1[O:1][CH:24]([C:25]#[N:26])[CH3:27])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5192252-ChloropropionitrileHCID 23665647Potassium tert-butoxideHCID 54725366HCID 54725366, compound

Product 1

HCID 53740933HCID 53740933, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of methyl 3-hydroxy-5-methoxybenzo[b]thiophene-2-carboxylate (1.00 g, 4.2 mmol) [Connor, et al., J. Med. Chem. 35:958 (1992)] in 20 mL of DMSO is added potassium t-butoxide (494 mg, 4.41 mmol) followed by 2-chloropropionitrile (1.1 mL, 12.6 mmol). The mixture is stirred at room temperature for 1.5 hours then warmed to 82° C. for 3 hours. The reaction mixture is poured into ethyl acetate and 1N HCl. The organic layer is washed with 1N HCl, followed by several portions of brine and dried over MgSO4. Filtration followed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate:hexane gives 853 mg, mp 127°-129° C.

Workup

  1. temperaturethen warmed to 82° C. for 3 hours
  2. washThe organic layer is washed with 1N HCl
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate
  6. customhexane gives 853 mg, mp 127°-129° C.

Sources & evidence

ORD record
ord-adff6b2f6d0c4002876aa2905f591c4a
Source dataset
uspto-grants-1996_10
Patent number
US05565446

Reaction notes

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