Benzoyl chloride → N-(1-Ethoxycyclopropyl)benzenecarboximidic acid

HRID 616976Notes

Reaction equation

HRID 616976 reaction equation
C(N(CC)CC)C.[Cl-].[CH2:9]([O:11][C:12]1([NH3+:15])[CH2:14][CH2:13]1)[CH3:10].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:9]([O:11][C:12]1([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH2:13]1)[CH3:10]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 20367034HCID 20367034, compound

Product 1

HCID 125108N-(1-Ethoxycyclopropyl)benzenecarboximidic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (2.5 g, 25 mmol) is added dropwise at 0° to a solution of 1-ethoxycyclopropylammonium chloride (1.25 g, 9.15 mmol) and benzoyl chloride (1.4 g, 10 mmol) in dry tetrahydrofuran (20 ml). The precipitate is filtered off and the filtrate is evaporated in vacuo yielding a crystalline residue. Sublimation following by recrystallisation from cyclohexane gives N-(1-ethoxycyclopropyl)-benzamide, mp 108°-109° (0.95 g, 51%); NMR (60 MHz): δCDCl 3 = 0.90-1.38 (m, 4H), 1.16 (t, J=7 Hz, 3H), 3.77 (q, J=7 Hz, 2H), 7.0-8.0 (1 m and 1 br. s, total 6H).

Workup

  1. filtrationThe precipitate is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. customyielding a crystalline residue
  4. customSublimation following by recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-c5bff4d1c3994bdab4a91ce598ed6d0d
Source dataset
uspto-grants-1978_02
Patent number
US04076840

Reaction notes

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