Allyl bromide → HCID 12016520, compound

HRID 1636849Notes

Reaction equation

HRID 1636849 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.[CH2:19]([Br:22])[CH:20]=[CH2:21]>CN(C=O)C>[Br-:22].[CH2:19]([N+:12]1([CH3:15])[CH2:13][CH2:14][N:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([NH2:1])[C:17]([Cl:18])=[CH:16][C:5]=3[N:6]=2)[CH2:10][CH2:11]1)[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 12016519HCID 12016519, compound

Product 1

HCID 12016520HCID 12016520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 50 mg portion of 6-amino-5-chloro-2-(4-methyl-1-piperazinyl)benzoxazole was dissolved in 5 ml of DMF, and the solution, while stirring at room temperature, was mixed with 135 mg of allyl bromide and stirred for additional 2 hours. Thereafter, the solvent was evaporated under a reduced pressure and the thus obtained mixture was purified by an LH-20 gel column chromatography (chloroform:methanol=1:1) to obtain the title compound (15 mg) in light yellow color. 1H-NMR (CD3OD) δ values: 3.17 (3 H, s), 3.5-3.7 (4 H, m), 3.8-4.2 (4 H, m), 4.13 (2 H, d), 5.65-5.8 (2 H, m), 6.0-6.15 (1 H, m), 6.93 (1 H, s), 7.20 (1 H, s); MS (EI): m/z 306 (M+)

Workup

  1. stirringstirred for additional 2 hours
  2. customThereafter, the solvent was evaporated under a reduced pressure
  3. customthe thus obtained mixture was purified by an LH-20 gel column chromatography (chloroform:methanol=1:1)

Sources & evidence

ORD record
ord-9163e62f918546c6a65dffe83a0c16f1
Source dataset
uspto-grants-2000_03
Patent number
US06037342

Reaction notes

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