Triethylamine → HCID 19422060, compound

HRID 744690Notes

Reaction equation

HRID 744690 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11]C=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].C(=O)(O)[O-].[Na+]>ClCCl>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:8][CH2:9][CH2:14][CH2:13][CH:12]([C:15]([F:16])([F:17])[F:18])[CH3:11])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 898486-Bromohexanoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 19422060HCID 19422060, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Triethylamine (1.30 mL) and 4-aminobenzotrifluoride (1.21 g) were stirred in dichloromethane (35 mL) at 0° C. under nitrogen and treated with 6-bromohexanoyl chloride (1.15 mL). After 20 minutes, the reaction was allowed to warm to 20° C. and stirred an additional 40 minutes. The reaction was treated with aqueous saturated sodium bicarbonate (40 mL), and extracted with dichloromethane. The extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to a solid. This solid was dissolved ethyl acetate and the title compound was precipitated out as fine white needles by addition of hexanes (2.35 g). M.p. 96°-98° C. Anal. Calc. for C13H15BrF3NO: C, 46.17;H, 4.47;N, 4.14. Found: C, 46.25;H, 4.59;N, 4.12.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a solid
  5. dissolutionThis solid was dissolved ethyl acetate
  6. customthe title compound was precipitated out as fine white needles by addition of hexanes (2.35 g)

Sources & evidence

ORD record
ord-8845e5dcf7b748c8ac2bd72a3cd390be
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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