N-bromobutanimide → 7-Bromo-2-methyl-4-benzoxazolamine

HRID 2110447Notes

Reaction equation

HRID 2110447 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([Br:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 106068972-Methyl-1,3-benzoxazol-4-amine

Product 1

HCID 218751637-Bromo-2-methyl-4-benzoxazolamineYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

Compound 474B (3.90 g, 26.3 mmol) was dissolved in DMF (45 mL) and cooled to −5° C. and N-bromosuccinimide (4.68 g, 26.3 mmol) was added in small portions and the reaction stirred for 5 h. The mixture was poured into 150 mL of ice water to give a cream colored solid which was filtered, washed with water, dissolved in CH2Cl2, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel eluting with 20% ether/CH2Cl2 gave compound 474C (3.36 g, 56%) as a beige solid. HPLC: 95.4% at 2.583 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 228.03 [M+H]+.

Workup

  1. customto give a cream colored solid which
  2. filtrationwas filtered
  3. washwashed with water
  4. dissolutiondissolved in CH2Cl2
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude material by flash chromatography on silica gel eluting with 20% ether/CH2Cl2

Sources & evidence

ORD record
ord-95c3c6e9228b4fecaf96acec0afb02ee
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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