Sodium amide → HCID 66848508, compound

HRID 2176154Notes

Reaction equation

HRID 2176154 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]([Br:21])=[CH:17][CH:16]=1>O1CCCC1>[Br: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 685274-Bromobenzyl bromideHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 66848508HCID 66848508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (253 mg, 6.15 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-bromobenzene (845 mg, 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) and extracted with dichloromethane (2×10 mL). 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 279 (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-26b5496cbb2b4222890eb9b352406db5
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

Loading…