Acetic Anhydride → N-[6-(3-Fluoro-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-acetamide

HRID 492088Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1.O>[F:23][C:19]1[CH:18]=[C:17]([S:14]([NH:13][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]([CH2:2][NH:1][C:24](=[O:26])[CH3:25])[CH2:12][CH2:11][CH2:10]3)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 0.18 grams (0.538 mmoles) N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-fluoro-benzenesulfonamide in 25 mL pyridine was added 0.052 grams (0.511 mmole) acetic anhydride. The reaction mixture was stirred at 23° C. for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with 0.5M hydrochloric acid, water, and saturated aqueous sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. N-[6-(3-Fluoro-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-acetamide was obtained as a crystalline solid from ethyl acetate/ethyl ether, 0.18 grams (89%), m.p. 136-137° C., M+H=377.

Workup

extractionextracted with ethyl acetate
washThe organic phase was washed with 0.5M hydrochloric acid, water, and saturated aqueous sodium chloride
dry with materialThe organic phase was dried (magnesium sulfate)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-58c13340c6cc47568021d2890df78cff
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531577B2

Reaction notes

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