Triethylamine → HCID 21833710, compound

HRID 1741071Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][C:3]=1[CH3:11].BrN1C(=O)[CH2:16][CH2:15][C:14]1=O.ClC(C)=C.C(N(CC)CC)C>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:14]=[C:15]([CH3:16])[O:8][N:7]=2)=[CH:4][C:3]=1[CH3:11]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 4-bromo-3-methylbenzaldehyde oxime (D81) (2.68 g, 0.0125 mol) in dry dimethylformamide (30 ml) was treated over 15 minutes with N-bromosuccinimide (636 mg, 0.00357 mol), and reaction mixture stirred for 2.5 hours, then cooled to -15° C. 2-Chloropropene (3.45 ml, 0.0405 mol) was added in a single portion, followed by dropwise addition of triethylamine (1.35 ml, 0.0097 mol) in dry dimethylformamide (10 ml) over 0.5 hours maintaining the temp. at -10° C. The mixture was stirred at 0° C. for 1 hour, then stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue partitioned between K2CO3 solution and chloroform. The organic phase was dried (Na2SO4) and evaporated under reduced pressure and the residue purified by chromatography on silica gel eluting with 60-80 petroleum-ether and ethyl acetate, to afford the title compound (246 mg, 8%).

Workup

temperaturemaintaining the temp
customat -10° C
stirringThe mixture was stirred at 0° C. for 1 hour
stirringstirred at room temperature overnight
customThe solvent was evaporated under reduced pressure
customthe residue partitioned between K2CO3 solution and chloroform
dry with materialThe organic phase was dried (Na2SO4)
customevaporated under reduced pressure
customthe residue purified by chromatography on silica gel eluting with 60-80 petroleum-ether and ethyl acetate

Sources & evidence

ORD record: ord-b61a16707a66440c9dfafb8938cc2f0e
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972951

Reaction notes

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