Ethylamine → HCID 58835358, compound

HRID 2224715Notes

Reaction equation

HRID 2224715 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]=[N+:27]=[N-:28])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(N)C>ClCCl>[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]=[N+:27]=[N-:28])(=[O:24])=[O:25])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 59717868HCID 59717868, compound

Product 1

HCID 58835358HCID 58835358, compoundYield 271.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the mixture of {2-[4-(4-azidosulfonylphenoxy)phenyl]ethyl} carbamic acid tert-butyl ester (0.291 g, 0.695 mmol) in dichloromethane (12 mL). Add TFA (12 mL) and stir at room temperature for 5 hours. Concentrate the reaction mixture. Load the product onto an SCX column with methanol. Wash the column with methanol then elute with 50% (2.0 M NH3 in methanol) in methanol to give a mixture of 2-4-(4-fluorobenzenesulfonyl)oxyphenyl)ethylamine and the title compound (0.601 g, 98.5%): MS ES+ 336.9 (M+H+18(NH4))+; TLC [silica gel 60 F254, 30% ethyl acetate,5% (2.0 M NH3 in methanol and 65% hexanes] Rf=0.034.

Workup

  1. dissolutionDissolve
  2. concentrationConcentrate the reaction mixture
  3. washWash the column with methanol
  4. washthen elute with 50% (2.0 M NH3 in methanol) in methanol
  5. customto give

Sources & evidence

ORD record
ord-d50a6136a9cb493a85597463feb27c6f
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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