Benzoyl chloride → HCID 20367038, compound

HRID 616974Notes

Reaction equation

HRID 616974 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[OH:11][C:12]1([NH3+:15])[CH2:14][CH2:13]1.C(N(CC)CC)C>O1CCCC1>[OH:11][C:12]1([NH:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 70620051HCID 70620051, compound

Product 1

HCID 20367038HCID 20367038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl chloride (4.2 g, 30 mmol) is added to a suspension of 1-hydroxycyclopropylammonium chloride (2.67 g, 24.5 mmol) in dry tetrahydrofuran. Triethylamine (6.5 g, 65 mmol) is added dropwise with stirring and ice-cooling (1 hr). The precipitate is filtered off and washed with tetrahydrofuran. The filtrate obtained is evaporated in vacuo. The crystalline residue is recrystallised from chloroform yielding N-(1-hydroxycyclopropyl)-benzamide, mp 153°-155° (3.0 g, 69%); NMR=δCDCl 3=0.87-1.38 (m, 4H), 4.7 (br. s, 1H), 7.3-7.9 (m, 6H, incl. NH).

Workup

  1. temperatureice-cooling (1 hr)
  2. filtrationThe precipitate is filtered off
  3. washwashed with tetrahydrofuran
  4. customThe filtrate obtained
  5. customis evaporated in vacuo
  6. customThe crystalline residue is recrystallised from chloroform

Sources & evidence

ORD record
ord-8daa1a3192e3419ebb71618e6796277f
Source dataset
uspto-grants-1978_02
Patent number
US04076840

Reaction notes

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