Hydrochloric Acid → 10,11-Dihydro-11-oxodibenzo[b,f][1,4]thiazepin-3-carboxylic acid

HRID 625179Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[C:10]1[CH:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].N1C2C(=CC=CC=2)C=CC=1.Cl>O.N1C=CC=CC=1>[O:20]=[C:19]1[C:17]2[CH:18]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][C:16]=2[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2-amino-benzenethiol (1.34 mL, 12.5 mmol), 2-bromo-terephthalic acid (1.54 g, 6.3 mmol), cuprous oxide (0.50 g, 3.5 mmol), quinoline (6.3 mL), and pyridine (0.63 mL) was heated in a 180° C. oil bath under nitrogen for 20 hours, then cooled to room temperature. Concentrated hydrochloric acid (20 mL) was added slowly while cooling in cold water, with stirring. The resulting precipitate was filtered, washed with water, and dried to give crude title compound (2 g). LC-MS: m/z 270 (M−1).

Workup

temperaturecooled to room temperature
filtrationThe resulting precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-5fb48b96ac7d4d4d8f5d1b2cbe2c0567
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09304126B2

Reaction notes

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