Benzoyl chloride → HCID 67059769, compound

HRID 1671282Notes

Reaction equation

HRID 1671282 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:19](Cl)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.[NH2:29][NH2:30].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[C:20]1([C:19]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[NH:29][N:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 10400CycloheptanoneHCID 24654Hydrazine hydrate (1:1)HCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 67059769HCID 67059769, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

Lithium hexamethyldisilazane (10 mL, 1.6 M tetrahyfuran solution, manufactured by Sigma-Aldrich Corp.) was added to a solution of cycloheptanone (561 mg, manufactured by Tokyo Chemical Industry Co., Ltd.) in toluene (10 mL, manufactured by Kanto Chemical Co., Inc.) at 0° C., and the mixture was stirred for one minute. Benzoyl chloride (90 μL, manufactured by Wako Pure Chemical Industries, Ltd.) was then added thereto at the same temperature, and the mixture was stirred for one hour. Subsequently, acetic acid (5 mL, manufactured by Wako Pure Chemical Industries, Ltd.) and hydrazine monohydrate (1 mL, manufactured by Tokyo Chemical Industry Co, Ltd.) were added to the reaction solution, and the mixture was stirred for 3 hours. A saturated aqueous solution of sodium carbonate (30 mL) was added to the reaction solution, and the mixture was extracted with (3×20 mL), washed with brine (40 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 230 mg of the title compound. LC-MS: HPLC retention time 1.57 minutes, m/z 213 (M+H), condition C-1.

Workup

  1. stirringat the same temperature, and the mixture was stirred for one hour
  2. stirringthe mixture was stirred for 3 hours
  3. extractionthe mixture was extracted with (3×20 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was then evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-99d1604f26d24388acc75149f1433d58
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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