Sodium amide → HCID 14591241, compound

HRID 2176153Notes

Reaction equation

HRID 2176153 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]([Cl:21])=[CH:17][CH:16]=1>O1CCCC1>[Cl: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 693291-(Bromomethyl)-4-chlorobenzeneHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 14591241HCID 14591241, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (202 mg, 4.92 mmol; Aldrich) and chilled to 0° C. (4-Fluorophenyl)hydrazine hydrochloride (400 mg, 2.46 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-chlorobenzene (556 mg, 2.7 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 234 (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. waitAfter 30 minutes
  6. customthe ice bath was removed
  7. additionThe mixture was diluted with water (5 mL)
  8. extractionextracted with dichloromethane (2×10 mL)
  9. dry with materialThe combined organic extracts were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2c63fdd9ee24419a29ae36cca15ba66
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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