Ammonium Chloride → HCID 178450043, compound

HRID 480469Notes

Reaction equation

HRID 480469 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([Li])(C)([CH3:9])[CH3:8].[CH:12]([C:14]1[CH:26]=[CH:25][C:24]2[C:16](=[CH:17][C:18]3[O:22][CH2:21][O:20][C:19]=3[CH:23]=2)[CH:15]=1)=[O:13].[Cl-].[NH4+]>C1COCC1.CCCCC>[NH:5]1[CH:6]=[C:2]([C:12]([C:14]2[CH:26]=[CH:25][C:24]3[C:16](=[CH:17][C:18]4[O:22][CH2:21][O:20][C:19]=4[CH:23]=3)[CH:15]=2)([OH:13])[CH:7]([CH3:9])[CH3:8])[N:3]=[CH:4]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 18769080HCID 18769080, compoundHCID 178418306HCID 178418306, compoundHCID 178418934HCID 178418934, compound

Product 1

HCID 178450043HCID 178450043, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromo-1H-imidazole (2.00 g) in THF (30 ml) was cooled to −78° C. A solution of tert-butyllithium in pentane (1.7 M; 22 ml) was added to the solution. The mixture was stirred at 0° C. for 1.5 h and then cooled to −78° C. 6-formylnaphtho[2,3-d][1,3]dioxol (3.00 g) in THF (30 ml) was added to the mixture. The mixture was allowed to room temperature and was stirred for 16 h. Ammonium chloride solution was added to the mixture and precipitate was collected, washed with water and ethyl acetate to give the titled compound (1.10 g) as a colorless solid.

Workup

  1. temperaturecooled to −78° C
  2. customwas allowed to room temperature
  3. stirringwas stirred for 16 h
  4. customwas collected
  5. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-df32314d6f3141d0879a7ae82c640664
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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