Oxalyl chloride → 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide

HRID 628009

Reaction equation

HRID 628009 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14]([OH:16])=O)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.[C:19]([Cl:24])(=O)[C:20](Cl)=O>ClCCl.CN(C=O)C>[Cl:24][C:19]1[CH:20]=[CH:3][CH:4]=[CH:5][C:6]=1[NH:7][C:14]([C:8]1[S:9][C:10]2[CH2:11][CH2:12][O:13][C:4]3[CH:3]=[C:2]([Br:1])[CH:18]=[CH:17][C:5]=3[C:6]=2[N:7]=1)=[O:16]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 579001668-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acid

Product 1

HCID 668689618-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (396 mg) in dry dichloromethane (20 mL) was added oxalyl chloride (180 μL) and DMF (1 drop). After 3 hours the solvent was removed in vacuo and to the residue was added acetonitrile (20 mL), 2-chloroaniline (140 μL) and sodium bicarbonate (111 mg). After 3 hours, water was added to the reaction mixture and the resulting precipitate was collected by filtration to yield 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide (467 mg).

Workup

  1. customAfter 3 hours the solvent was removed in vacuo and to the residue
  2. additionwas added acetonitrile (20 mL), 2-chloroaniline (140 μL) and sodium bicarbonate (111 mg)
  3. additionwater was added to the reaction mixture
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-eb99534d233b431da981e8e187c8b2e9
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Linked notes

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