Sodium Hydroxide → HCID 15085962, compound

HRID 1073266Notes

Reaction equation

HRID 1073266 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=O>O.C(O)C>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:13])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2365665-FluoroisatinHCID 131716686HCID 131716686, compound

Product 1

HCID 15085962HCID 15085962, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
80 °C

Procedure

To a suspension of 526 mg of 5-fluoroisatin in 4 ml of water was added 737 mg of sodium hydroxide in 6 ml of water. The resulting solution was heated to 80° C., then a solution of 1.254 g of 2-amino-1-[4-(phenylthio)phenyl]ethanone, hydrochloride in 8 ml of ethanol and 8 ml of water was added dropwise. After heating at reflux for 1 hour, the volatiles were removed in vacuo, 10 ml of water was added and the mixture filtered. A 60 ml portion of water was added to the filtrate which was then acidified to pH 4 with glacial acetic acid. After stirring for 25 minutes the solid was collected, washed with water and crystallized from 50 ml of hot acetonitrile, giving 442 mg of the desired product, mp 219°-221° C. (dec.).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1 hour
  3. customthe volatiles were removed in vacuo, 10 ml of water
  4. additionwas added
  5. filtrationthe mixture filtered
  6. additionA 60 ml portion of water was added to the filtrate which
  7. customwas collected
  8. washwashed with water
  9. customcrystallized from 50 ml of hot acetonitrile

Sources & evidence

ORD record
ord-aedf9334f3684dac8a55e4e1f0c0627b
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

Loading…