Trifluoroacetic acid → 2-[2-(6-Chlorohexyloxy)ethoxy]ethylammonium trifluoroacetate

HRID 402212

Reaction equation

HRID 402212 reaction equation
C1C2C(=CC3C(C=2COC(=O)[NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=CC=CC=3)C=CC=1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl.C1(OC)C=CC=CC=1>[F:33][C:34]([F:39])([F:38])[C:35]([O-:37])=[O:36].[Cl:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH3+:18]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10072837{2-[2-(6-Chloro-hexyloxy)-ethoxy]-ethyl}-carbamic acid anthracen-9-ylmethyl ester

Product 1

HCID 866717092-[2-(6-Chlorohexyloxy)ethoxy]ethylammonium trifluoroacetate

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6344DichloromethaneSolvent

Procedure

To {2-[2-(6-Chloro-hexyloxy)-ethoxy]-ethyl}-carbamic acid anthracen-9-ylmethyl ester (0.56 g, 1.2 mmol) dissolved in 4 ml dichloromethane was added 2 drops of anisole. The reaction mixture is cooled by means of an ice/NaCl bath. After 10 minutes trifluoroacetic acid (2 ml) is added. The reaction mixture turns dark brown upon addition and is allowed to stir for 30 minutes. All volatiles are removed under reduced atmosphere. The residue is re-dissolved in CH2Cl2 and washed twice with water. The aqueous fractions are frozen and lyophilized overnight. An oily residue remains and is dissolved in anhydrous DMF to be used as a stock solution in further reactions. Mass spectrum, m/e Calcd for C10H23ClNO2+: 224.14 (100%), 226.14 (32%). Found: 224.2, 226.2.

Workup

  1. temperatureThe reaction mixture is cooled by means of an ice/NaCl bath
  2. additionThe reaction mixture turns dark brown upon addition
  3. customAll volatiles are removed under reduced atmosphere
  4. dissolutionThe residue is re-dissolved in CH2Cl2
  5. washwashed twice with water
  6. temperatureThe aqueous fractions are frozen
  7. waitlyophilized overnight
  8. dissolutionis dissolved in anhydrous DMF

Sources & evidence

ORD record
ord-6b1d5d2691754a139b94785962276215
Source dataset
uspto-grants-2014_06
Patent number
US08742086B2

Linked notes

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