Sodium amide → HCID 66848663, compound

HRID 2176158Notes

Reaction equation

HRID 2176158 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[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1>O1CCCC1>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:18][CH:19]=2)[NH2:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 534214634-(Bromomethyl)-2-phenyl-1,3-oxazole

Product 1

HCID 66848663HCID 66848663, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (152 mg, 3.69 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 4-(bromomethyl)-2-phenyloxazole (586 mg, 2.46 mmol; Anichem) 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 267 (M+H−NH3)+.

Workup

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

Sources & evidence

ORD record
ord-a7eaaf5f84414eec9e2f4e981112a5e4
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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