Triethylamine → HCID 2725909, compound

HRID 538420Notes

Reaction equation

HRID 538420 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Br.Br[CH2:16][CH2:17][NH2:18].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][CH2:16][CH2:17][N:18]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 2725909HCID 2725909, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(trifluoromethyl)benzoyl chloride (4.6 mL, 31 mmol) was slowly added to a solution of 2-bromoethanamine hydrobromide (6.27 g, 30.6 mmol) and triethylamine (23 mL, 165 mmol) in dry DCM (150 mL) at 0° C. The reaction was stirred for 18 h, allowing the cooling bath to expire. The resulting mixture was filtered through a Buechner funnel and the filter cake was washed thoroughly with DCM. The collected filtrate was washed with water (100 mL), brine (75 mL), and dried (Na2SO4). The volume was reduced in vacuo to 5 mL and the resulting crystals were harvested. The remaining filtrate was again reduced in volume to provide a second crop of crystals to give a total of 4.8 g of 2-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole. The combined crop of crystals were dissolved in CCl4 (200 mL) and the resulting solution was decanted away from a dark oily residue and was carried forward without further purification: LC/MS (m/z): 216.1 (MH+), tR=0.60 min.

Workup

  1. filtrationThe resulting mixture was filtered through a Buechner funnel
  2. washthe filter cake was washed thoroughly with DCM
  3. washThe collected filtrate was washed with water (100 mL), brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. customto provide a second crop of crystals

Sources & evidence

ORD record
ord-3938de777cf04300872fb24ce941631c
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

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