Dichloromethane → HCID 86608217, compound

HRID 1782100Notes

Reaction equation

HRID 1782100 reaction equation
C(Cl)Cl.[N:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N+:5]=[N-:6].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH:25]=O)=[CH:23][N:22]=[CH:21]2)=[CH:16][CH:15]=1.[O-]CC.[K+]>C(O)C>[N:4]([C:7](=[CH:25][C:24]1[N:20]([C:17]2[CH:18]=[CH:19][C:14]([Br:13])=[CH:15][CH:16]=2)[CH:21]=[N:22][CH:23]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N+:5]=[N-:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 69480Acetic acid, azido-, ethyl esterHCID 18005593HCID 18005593, compoundHCID 23670592Potassium ethoxide

Product 1

HCID 86608217HCID 86608217, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A commercially available 34% methylene chloride solution of ethyl azidoacetate (6.6 mL, 21.6 mmol) was concentrated in vacuo, the residue reconstituted in anhydrous ethanol (100 mL) and the resulting solution treated with 3-(4-bromophenyl)-3H-imidazole-4-carbaldehyde (6) (2.7 g, 10.8 mmol). The mixture was cooled to 0° C., treated dropwise with potassium ethoxide solution (5.1 mL, 13.0 mmol, 24% (w/w) EtOH solution) and the mixture stirred at 0° C. for 5 h. The resulting white solid was collected by filtration and dried in air to yield ethyl 2-azido-3-[3-(4-bromophenyl)-3H-imidazol-4-yl]acrylate (7). LC-MS (ES+): m/z 362/364 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=1.31 (t, J=7.1 Hz, 3H), 4.30 (q, J=7.1 Hz, 2H), 6.52 (d, J=0.7 Hz, 1H), 7.19 (d, J=8.7 Hz, 2H), 7.67 (s, 1H), 7.68 (d, J=8.7 Hz, 2H), 8.03 (d, J=0.7 Hz, 1H).

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. customdried in air

Sources & evidence

ORD record
ord-d3d304294c004309891cd15c622547b4
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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