Pyridine → HCID 22287299, compound

HRID 2301030Notes

Reaction equation

HRID 2301030 reaction equation
C([O:4][C:5]([CH3:10])([CH3:9])[C:6](Cl)=[O:7])(=O)C.[F:11][C:12]1[CH:18]=[C:17]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:13]=1[NH2:14].N1C=CC=CC=1>C(Cl)Cl>[F:11][C:12]1[CH:18]=[C:17]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:13]=1[NH:14][C:6](=[O:7])[C:5]([OH:4])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 22287222HCID 22287222, compound

Product 1

HCID 22287299HCID 22287299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Acetoxy-2-methylpropanoyl chloride (0.47 ml) was added to a solution of 2-fluoro-4-phenylsulphanylaniline (Method 7) (0.64 g) and pyridine (0.28 ml) in DCM (10 ml). The solution was stirred at ambient temperature for 90 minutes then volatile material was removed by evaporation. The residue was dissolved in methanol (20 ml and a solution of lithium hydroxide monohydrate (0.378 g) in water (2.5 ml) was added. Stirring was continued for another 1 hour then the mixture was acidified to pH 1 with 2M hydrochloric acid and concentrated by evaporation to about 5 ml. Water (10 ml) was added and the product was extracted with ethyl acetate. Organic layers were washed with brine then combined and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 10-20% ethyl acetate/hexane to yield the title compound (0.784 g) as a solid. Mp 91-92.5° C.; NMR: 1.34 (s, 6H), 5.96 (s, 1H), 7.15 (d, 1H), 7.23 (dd, 1H), 7.27-7.4 (m, 5H), 8.02 (t, 1H), 9.3 (s, 1H); MS (ESP−): 304; EA: found: C, 62.8; H, 5.3; N, 4.5; S, 10.5%; C16H16FNO2S requires: C, 62.9; H, 5.3; N, 4.6; S, 10.5%.

Workup

  1. customvolatile material was removed by evaporation
  2. dissolutionThe residue was dissolved in methanol (20 ml
  3. additiona solution of lithium hydroxide monohydrate (0.378 g) in water (2.5 ml) was added
  4. stirringStirring
  5. waitwas continued for another 1 hour
  6. concentrationconcentrated by evaporation to about 5 ml
  7. additionWater (10 ml) was added
  8. extractionthe product was extracted with ethyl acetate
  9. washOrganic layers were washed with brine
  10. customdried
  11. customVolatile material was removed by evaporation
  12. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  13. washeluting with 10-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7d0cb1115a6143959c432f523a7ed761
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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