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

HRID 625179
Notes
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Reaction equation

HRID 625179 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 87132-AminothiophenolHCID 68513Bromoterephthalic acid

Product 1

HCID 1301392310,11-Dihydro-11-oxodibenzo[b,f][1,4]thiazepin-3-carboxylic acidYield 117%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 1049PyridineSolvent

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

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes