Triethylamine → Methyl-N-(5-bromo-1-naphthoyl)-2-(1-naphthalenyl)acetimidate

HRID 2232059Notes

Reaction equation

HRID 2232059 reaction equation
Cl.[CH3:2][O:3][C:4](=[NH:16])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[Br:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[C:35](Cl)=[O:36]>C1(C)C=CC=CC=1>[CH3:2][O:3][C:4](=[N:16][C:35]([C:30]1[C:31]2[C:26](=[C:25]([Br:24])[CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:28][CH:29]=1)=[O:36])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27718835-Bromonaphthalene-1-carbonyl chlorideHCID 1986396439739-56-5

Product 1

HCID 19863963Methyl-N-(5-bromo-1-naphthoyl)-2-(1-naphthalenyl)acetimidateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the procedure of Soto et al, Synthesis, 483, (1983), to a stirred suspension of methyl-2-(1-naphthalenyl)acetimidate hydrochloride (prepared in Step 1) (11.7 g, 0.050 mol), in dry toluene (150 mL) was added triethylamine (11.5 g, 0.114 mol). 5-Bromo-1-naphthoyl chloride (13.4 g, 0.050 mol) was added in one portion and the resulting mixture was stirred at room temperature for 16 hours. The precipitated salt was removed by filtration and washed with toluene. The filtrate was concentrated in vacuo to give an orange oil (21.5 g, 100%) which was used without purification.

Workup

  1. customThe precipitated salt was removed by filtration
  2. washwashed with toluene
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a52949361f3d4f2ea8fee6b132bfaccf
Source dataset
uspto-grants-1988_11
Patent number
US04786640

Reaction notes

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