Chlorosuccinimide → HCID 11683023, compound

HRID 854482Notes

Reaction equation

HRID 854482 reaction equation
[CH2:1]([N:8]([CH2:25][CH3:26])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:34])C(=O)C1>CC(O)C>[CH2:1]([N:8]([CH2:25][CH3:26])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:16]([F:17])([F:18])[F:19])[C:20]([F:21])([F:22])[F:23])=[CH:11][C:10]=1[Cl:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11574384HCID 11574384, compound

Product 1

HCID 11683023HCID 11683023, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 20 mg (0.05 mmol) of 2-[4-(benzyl-ethyl-amino)-phenyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 1.2) in 0.5 mL of 2-propanol was treated with 7 mg (0.05 mmol) of NCS. The mixture was stirred at 80° C. for 10 hours and the solvent was evaporated. Column chromatography on silicagel with n-heptane/EtOAc 9:1 yielded 17 mg (82%) of 2-[4-(benzyl-ethyl-amino)-3-chloro-phenyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol, colorless oil, MS: 412 (MH+, 1Cl).

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-62e31b6a8b07463bb6510ac3a9397900
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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