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Methylamine → HCID 11391445, compound

HRID 1838900
Notes
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Reaction equation

HRID 1838900 reaction equation
[CH3:1][NH2:2].IC[CH2:5][CH2:6][CH:7]([S:17][CH:18](CCCI)[CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])CCC(F)(F)C(F)(F)F>O1CCCC1>[CH3:1][NH:2][CH2:5][CH2:6][CH2:7][S:17][CH2:18][CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6329MethylamineHCID 865876413-Iodopropyl-4,4,5,5,5-pentafluoropentylsulfide

Product 1

HCID 11391445HCID 11391445, compoundYield 133.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

45 g of methylamine are condensed at a bath temperature of −78° C. into a solution of 30.6 g of 3-iodopropyl-4,4,5,5,5-pentafluoropentyl sulphide in 200 ml of abs. tetrahydrofuran and the mixture is stirred at room temperature for 1.5 hours and at 60° C. for 4 hours in a pressure reactor. To open the reactor, it is allowed to cool overnight to room temperature and then to −78° C. It is then allowed to come to room temperature, excess methylamine is evaporated, the mixture is diluted with ethyl acetate, washed until neutral, dried over sodium sulphate and concentrated in vacuo, and the residue is chromatographed on silica gel using dichloromethane/methanol. 15.7 g of N-methyl-[3-(4,4,5,5,5-pentafluoro-pentylthio)propyl]amine are obtained as an oil.

Workup

  1. temperatureto cool overnight to room temperature
  2. customto −78° C
  3. customto come to room temperature
  4. customexcess methylamine is evaporated
  5. additionthe mixture is diluted with ethyl acetate
  6. washwashed until neutral,
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-3b7e9b58bee244ae8ebaf4ae893669c7
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06677324B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes