Succinic anhydride → 3-(4,5,7-Trifluorobenzothiazol-2-yl)propionic acid

HRID 1940610Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[SH:11].[C:12]1(=O)[O:17][C:15](=[O:16])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CN1C(=O)CCC1>[F:8][C:7]1[C:2]2[N:1]=[C:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:11][C:3]=2[C:4]([F:10])=[CH:5][C:6]=1[F:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-amino-3,4,6-trifluorothiophenol (1.79 g, 10 mmol) in NMP (5 ml) was added dropwise a solution of succinic anhydride (1.0 g, 10 mmol) in NMP (5 ml) at ambient temperature under a nitrogen stream and the mixture was heated to 100° C. for 1 hour. The resultant mixture was basified by dilution with aqueous sodium carbonate and washed with ether. The aqueous layer was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield crude crystals, which were washed with hexane-isopropyl ether to give 3-(4,5,7-trifluorobenzothiazol-2-yl)propionic acid 2.16 g, 83%).

Workup

washwashed with ether
extractionextracted with ethyl acetate
washThe organic layer was washed with water
customdried
customevaporated
customto yield crude crystals, which
washwere washed with hexane-isopropyl ether

Sources & evidence

ORD record: ord-20d866f4e5b646daacf29ca62ccc8cd8
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05700819

Reaction notes

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