5,6-difluoro-2,3-dihydro-1H-indole-2,3-dione → 5-Fluoro-6-methylthioindole-2,3-dione

HRID 844207Notes

Reaction equation

HRID 844207 reaction equation
[CH3:1][S-:2].[Na+].[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1F)[NH:10][C:9](=[O:15])[C:8]2=[O:16]>CN(C)C=O>[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[S:2][CH3:1])[NH:10][C:9](=[O:15])[C:8]2=[O:16]

Participants

4

Reactant 2

HCID 19263085,6-difluoro-2,3-dihydro-1H-indole-2,3-dioneHCID 4378561Sodium methanethiolate

Product 1

HCID 226127305-Fluoro-6-methylthioindole-2,3-dioneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (5.93 g, 84.6 mmol) was added to a solution of 5,6-difluoroindole-2,3-dione (7.75 g, 42.3 mmol) in dimethylformamide (400 mL). The reaction was stirred at room temperature for 1 h, then poured onto ice (2 L). The resulting solid was collected by filtration, washed with water and dried at 40° C. under vacuum to give a brown solid (3.12 g, 35%): mp 296° C.; C9H6F1NO2S requires: C, 51.18; H, 2.86; N, 6.63; S, 15.18%. Found C, 50.95; H, 2.85; N, 6.58; S, 15.35%; IR νmax (Nujol)/cm−1 3285, 2925, 2854, 1760, 1714, 1611, 1465 and 1036; NMR δH (400 MHz, DMSO-d6) 2.58 (3H, s), 6.71 (1H, d, J 6.0 Hz), 7.38 (1H, d, J 9.0 Hz), 11.02 (1H, brs).

Workup

  1. additionpoured onto ice (2 L)
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-11130431320c4b0088c59d37b6230fcd
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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