Hydrochloric Acid → HCID 68689924, compound

HRID 1160379Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+].Cl>C(#N)C>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 20 °C

Procedure

1 g of methyl 2-[3-(2-aminophenyl)propyl]benzoate obtained in Example 5 (3.7 mM), 0.71 g of 4-methylphenylsulfonyl chloride (3.7 mM) and 34 mg of NaHCO3 (4.1 mM) are added to 15 ml of acetonitrile in a 50 ml reactor. The reaction medium is stirred at 20° C. for 20 hours. 5 ml of 1M HCl are then added and the mixture is extracted with ethyl acetate. The organic phase is separated out after settling of the phases, washed and then dried over Na2SO4. After evaporation under vacuum, an oil is obtained, which is precipitated from ethyl ether. The solid is filtered off and washed with ether. 0.42 g of a grey-white solid is obtained (yield: 27%).

Workup

extractionthe mixture is extracted with ethyl acetate
customThe organic phase is separated out
washwashed
dry with materialdried over Na2SO4
customAfter evaporation under vacuum
customan oil is obtained
customwhich is precipitated from ethyl ether
filtrationThe solid is filtered off
washwashed with ether

Sources & evidence

ORD record: ord-4539eba7cd9a41c3aa6b779033e11a3a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816397B2

Reaction notes

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