Triethylamine → HCID 15388980, compound

HRID 2082555Notes

Reaction equation

HRID 2082555 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][CH:10]=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][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)=[O:26]

Participants

6

Reactant 4

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

Product 1

HCID 15388980HCID 15388980, 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 in 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.

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 in 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-828dd92a3db048dca4168719f274d6c4
Source dataset
uspto-grants-1993_02
Patent number
US05189179

Reaction notes

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