Benzoyl chloride → HCID 20367050, compound

HRID 616975Notes

Reaction equation

HRID 616975 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[CH3:18][O:19][C:20]1([NH3+:23])[CH2:22][CH2:21]1>O1CCCC1>[CH3:18][O:19][C:20]1([NH:23][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2036704958939-47-2

Product 1

HCID 20367050HCID 20367050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (3.1 g, 30.5 mmol) is added dropwise (30 min) at 0° to a solution of benzoyl chloride (1.5 g, 12.2 mmol) in tetrahydrofuran (25 ml) containing suspended 1-methoxycyclopropylammonium chloride (1.82 g, 13.0 mmol). The mixture is then stirred at room temperature for 30 min. The precipitate is filtered off and washed thoroughly with tetrahydrofuran. The filtrate is evaporated in vacuo yielding a crystalline residue. Recrystallisation from methanol gives pure N-(-methoxycyclopropyl)-benzamide, mp 190°-191° (1.2 g, 55%); NMR (60 MHz)=δCDCl 3=1.00-1.30 (m, 4H), 3.40 (s, 3H), 7.0 (br. s, 1H), 7.35-7.95 (m, 5H).

Workup

  1. additioncontaining
  2. filtrationThe precipitate is filtered off
  3. washwashed thoroughly with tetrahydrofuran
  4. customThe filtrate is evaporated in vacuo
  5. customyielding a crystalline residue
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-f55480f8f1a94680805d99ddadb084d8
Source dataset
uspto-grants-1978_02
Patent number
US04076840

Reaction notes

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