Ammonia → HCID 59295975, compound

HRID 2233391Notes

Reaction equation

HRID 2233391 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[C:16]=2[S:23](Cl)(=[O:25])=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C.[NH3:27]>CO>[Cl:22][C:17]1[C:18]([Cl:21])=[CH:19][CH:20]=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:16]=1[S:23]([NH2:27])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59295944HCID 59295944, compound

Product 1

HCID 59295975HCID 59295975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl-4-[3,4-dichloro-2-(chlorosulfonyl)phenoxy]piperidine-1-carboxylate (0.80 g, 1.8 mmol) was dissolved in 7N ammonia in methanol and stirred at room temperature for 20 min. The solution was concentrated in vacuo and then azeotroped once with toluene. The residue was redissolved in dichloromethane:trifluoroacetic acid/1:1 (20 ml) and stirred at room temperature for 15 minutes. The solution was concentrated in vacuo, then partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The aqueous was reextacted with ethyl acetate (4 times), and the combined organics dried over anhydrous potassium carbonate. Concentration in vacuo afforded the title compound as a white powder (0.54 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customazeotroped once with toluene
  3. dissolutionThe residue was redissolved in dichloromethane
  4. stirringtrifluoroacetic acid/1:1 (20 ml) and stirred at room temperature for 15 minutes
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialthe combined organics dried over anhydrous potassium carbonate
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-cfc3288bfb4a47b1b725a66aa703451b
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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