Heptane → 4-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl chloride
Reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:25])[NH:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]O)=[CH:17][C:16]=1[O:23][CH3:24].CCCCCCC>ClCCl>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:25])[NH:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][Cl:3])=[CH:17][C:16]=1[O:23][CH3:24]Participants
Procedure
7.65 ml (104.8 mmol) of thionyl chloride were added dropwise with ice cooling to a suspension of 15 g (52.4 mmol) of 4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl alcohol in 300 ml of dichloromethane. The reaction mixture was subsequently stirred at room temperature for 3 hours, allowed to stand overnight and then poured onto 1000 ml of n-heptane. The heptane was decanted off from the deposited oil, the residue was again suspended with n-heptane and the heptane was decanted off. This process was repeated a further two times. The residue was then dissolved in dichloromethane and poured into 800 ml of ice-cold diisopropyl ether. It was subsequently stirred with ice cooling for 2 hours, and the product was filtered off with suction and washed with diisopropyl ether. After drying over phosphorus pentoxide, 12 g (75%) of the title compound were obtained.
Workup
- waitto stand overnight
- customThe heptane was decanted off from the deposited oil
- customthe heptane was decanted off
- dissolutionThe residue was then dissolved in dichloromethane
- additionpoured into 800 ml of ice-cold diisopropyl ether
- stirringIt was subsequently stirred with ice cooling for 2 hours
- filtrationthe product was filtered off with suction
- washwashed with diisopropyl ether
- dry with materialAfter drying over phosphorus pentoxide
Sources & evidence
- ORD record
- ord-b50a38f122074b33b20512ac5d64a620
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06399643B1
Reaction notes
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