Sodium amide → HCID 66848113, compound

HRID 2176152Notes

Reaction equation

HRID 2176152 reaction equation
[NH2-].[Na+].Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1>O1CCCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)[NH2:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 680214-Fluorobenzyl bromideHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 66848113HCID 66848113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (89 mg, 4.61 mmol; Aldrich) and chilled to 0° C. (4-Fluorophenyl)hydrazine hydrochloride (500 mg, 3.08 mmol; Aldrich) was added in portions. After 5 minutes the solid had completely dissolved and the ice bath was removed. Stirring was continued for 1 hour, then the solution was chilled again in an ice bath and 1-(bromomethyl)-4-fluorobenzene (0.416 mL, 3.38 mmol; Aldrich) was added dropwise. After 30 minutes the ice bath was removed and the reaction was heated to 50° C. overnight. The mixture was diluted with water (5 mL), extracted with dichloromethane (2×10 mL) and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product which was carried on without further purification: LC/MS (DCI/NH3) m/z 218 (M+H−NH3)+.

Workup

  1. additionwas added in portions
  2. dissolutionAfter 5 minutes the solid had completely dissolved
  3. customthe ice bath was removed
  4. temperaturethe solution was chilled again in an ice bath
  5. customAfter 30 minutes the ice bath was removed
  6. additionThe mixture was diluted with water (5 mL)
  7. extractionextracted with dichloromethane (2×10 mL)
  8. dry with materialthe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4ae885ae1294b0583ff092f4aeebd3a
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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