Chlorosuccinimide → HCID 13339542, compound

HRID 1723561Notes

Reaction equation

HRID 1723561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].ClN1C(=[O:25])CCC1=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]2=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13339549HCID 13339549, compound

Product 1

HCID 13339542HCID 13339542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-(3-Fluoro-4-methoxyphenyl)indole (7.0 g, 0.029 mole, N-chlorosuccinimide (98%, 4.14 g, 0.0304 mole) and CH2Cl2 (200 ml) were combined and stirred 2 hours at 25° C., producing a solution which was evaporated in vacuo to a semisolid. The latter was diluted with 120 ml CH3CO2H and warmed to 70°. H3PO4 (85%, 31.3 ml) was added in one portion, the mixture was refluxed 1 hour, cooled, basified with saturated Na2CO3 and extracted 4×100 ml ethyl acetate. The organic layers were combined, dried over MgSO4, and evaporated in vacuo to solids (7.9 g). Chromatography on silica gel, (7.5×15 cm) eluting with CH2Cl2 in 1 liter fractions gave, on evaporation of combined fractions 4-13, purified title product, 3.8 g, m.p. 133°-136°.

Workup

  1. customproducing a solution which
  2. customwas evaporated in vacuo to a semisolid
  3. additionThe latter was diluted with 120 ml CH3CO2H
  4. temperaturewarmed to 70°
  5. additionH3PO4 (85%, 31.3 ml) was added in one portion
  6. temperaturethe mixture was refluxed 1 hour
  7. temperaturecooled
  8. extractionextracted 4×100 ml ethyl acetate
  9. dry with materialdried over MgSO4
  10. customevaporated in vacuo to solids (7.9 g)
  11. washChromatography on silica gel, (7.5×15 cm) eluting with CH2Cl2 in 1 liter fractions
  12. customgave, on evaporation of combined fractions 4-13
  13. custompurified title product, 3.8 g, m.p. 133°-136°

Sources & evidence

ORD record
ord-1bc5034eb30e4c36adde7d1f5da93379
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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