Benzoyl chloride → HCID 86610255, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[C:29]([N:8]([CH2:9][C:10]1([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:11][CH2:12]1)[C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
10.17 g of the compound obtained in Step 1 of Example 9 are dissolved in 200 ml of tetrahydrofuran, 4.88 ml of triethylamine are added, cooling to 5° C. is carried out and, over a period of 30 minutes, 5.05 g of benzoyl chloride are poured in. Stirring is carried out for one hour at 5° C. and then for one hour at ambient temperature, and subsequently refluxing is carried out for 2 hours. Concentration to dryness is carried out and the residue is taken up in dichloromethane and washed with 50% aqueous potassium carbonate solution. The organic phase is dried over sodium sulphate and concentrated, and chromatography of the residue on silica gel (dichloromethane/tetrahydrofuran: 96/4) allows 13.9 g of expected product to be obtained.
Workup
- waitis carried out for one hour at 5° C.
- waitfor one hour at ambient temperature
- temperaturesubsequently refluxing
- waitis carried out for 2 hours
- concentrationConcentration to dryness
- washwashed with 50% aqueous potassium carbonate solution
- dry with materialThe organic phase is dried over sodium sulphate
- concentrationconcentrated
- customto be obtained
Sources & evidence
- ORD record
- ord-8edd5818878249f0b8e32bcf3ac78741
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07388022B2
Reaction notes
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