Benzoyl chloride, 3,4-dichloro- → HCID 22807733, compound

HRID 262271Notes

Reaction equation

HRID 262271 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH3:15])[C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20](Cl)=[O:21]>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20]([NH:14][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[N:7]([CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH3:15])=[O:21]

Participants

3

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 22807734HCID 22807734, compound

Product 1

HCID 22807733HCID 22807733, compoundYield 50%

Procedure

This titled benzamide was prepared according to the general acid chloride method described above on a 0.01 mol scale by reacting the trans-2-[N-(2-furylmethyl)methylamino]cyclohexylamine, prepared as described in part (a) above with 3,4-dichlorobenzoyl chloride. The reaction product mixture was extracted with methylene dichloride to extract the benzamide product therefrom. The crude product was chromatographed on 380 g. of silica gel using a 1 percent methanol-in-chloroform eluant. Fraction 1 (1000 m.) and fractions 2 to 17 (25 ml. each) gave no material. Fractions 18 to 54 (25 ml. each) gave a solid which was crystallized from ether giving colorless needles, 1.91 g., (50% yield) of the named benzamide product, melting point 149°-150° C. The Ultraviolet, Infrared, and Nuclear Magnetic Resonance spectral analyses were consistent for the named benzamide.

Workup

  1. customThis titled benzamide was prepared
  2. customprepared
  3. extractionThe reaction product mixture was extracted with methylene dichloride
  4. extractionto extract the benzamide product
  5. customThe crude product was chromatographed on 380 g
  6. customeach) gave no material
  7. customeach) gave a solid which
  8. customwas crystallized from ether giving colorless needles, 1.91 g

Sources & evidence

ORD record
ord-5331ac09800841928cca734a4d5b82af
Source dataset
uspto-grants-1979_05
Patent number
US04153717

Reaction notes

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