(Diethylamino)sulfur trifluoride → HCID 18544602, compound

HRID 1268415Notes

Reaction equation

HRID 1268415 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH2:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[O:20])=[CH:17][CH:16]=1)[CH:7]2O.C(N(S(F)(F)[F:37])CC)C.C([O-])(O)=O.[K+]>C(Cl)Cl>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH2:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[O:20])=[CH:17][CH:16]=1)[CH:7]2[F:37]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516893Potassium BicarbonateHCID 18544613HCID 18544613, compound

Product 1

HCID 18544602HCID 18544602, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-65 °C

Procedure

A solution containing 0.35 g of 4-[(5,6-dichloro-1-hydroxy-1,2,3,4-tetrahydro-2-naphthalenyl)methyl]-N-(2-methylphenyl)benzamide and 10 cm3 of methylene chloride is cooled down to −65°C.±5° C. 142 mg of DAST (diethylaminosulfur trifluoride) was added. The solution was maintained under agitation for 1 hour at −65° C. The temperature was allowed to rise to 20° C. and the reaction medium was poured into an aqueous solution of potassium acid carbonate, followed by agitation for 30 minutes and extraction with methylene chloride. The organic phases were collected, dried, filtered and concentrated. In this way 340 mg of sought product was obtained.

Workup

  1. temperatureis cooled down to −65°C.±5° C
  2. customto rise to 20° C.
  3. extractionextraction with methylene chloride
  4. customThe organic phases were collected
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3b663885bab54453b23391ff5d96f108
Source dataset
uspto-grants-2003_04
Patent number
US06555709B1

Reaction notes

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