Dimethylformamide → HCID 87283339, compound

HRID 1869706Notes

Reaction equation

HRID 1869706 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].CN(C)C=O.[CH2:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13]>O>[CH:1]([NH:4][CH2:10][CH:11]([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 914503,3,3-Trifluoro-2-(trifluoromethyl)-1-propene3×

Product 1

HCID 87283339HCID 87283339, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of isopropylamine (5.65 g) and dimethylformamide (DMF, 5 mL) was added HFIB in several portions over a period of about 0.5 h until a gentle reflux of HFIB was observed which did not dissipate. A dry-ice condenser was used to obtain the gentle reflux of HFIB at 25° C. for 15 h. The reaction mixture was poured into water (100 mL) and the bottom layer separated, washed with water (10 mL) and dried over sodium sulfate to provide N-isopropyl N-(2-trifluoromethyl-3,3,3-trifluoropropyl)amine (15 g): MS (m/e) 223 (M+, 1.2%), 208 (100%), 72 (7.8%); 1H NMR (CDCl3) 1.06 (d, J=6 Hz, 6H), 1.12 (m, 1H), 2.81 (m, 1H), 3.07 (m, 3H) ppm; 19F NMR −67.0 (d, J=9 Hz) ppm.

Workup

  1. customA dry-ice condenser was used
  2. customto obtain the
  3. customthe bottom layer separated
  4. washwashed with water (10 mL)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-996a0ae7cee4435399ebc22f5ade79f9
Source dataset
uspto-grants-2009_12
Patent number
US07638650B2

Reaction notes

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