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o-Phenylenediacetic acid → HCID 9909006, compound

HRID 1358756
Notes
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Reaction equation

HRID 1358756 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=O.[F:21][C:22]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1)(=[O:27])=[O:26])([F:24])[F:23]>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[F:23][C:22]([F:21])([F:24])[S:25]([C:28]1[CH:29]=[C:30]([NH:34][C:14]([CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:17][C:18]([OH:20])=[O:19])=[O:16])[CH:31]=[CH:32][CH:33]=1)(=[O:26])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24123o-Phenylenediacetic acidHCID 65578Oxalyl chlorideHCID 27359433-Aminophenyl trifluoromethyl sulfone

Product 1

HCID 9909006HCID 9909006, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalyst
HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.285 mL) was added to a solution of 1,2-phenylenediacetic acid (100 mg, 0.515 mmol) in dichloromethane, followed by 5 drops of DMF. The mixture was stirred at room temperature for 1.5 hours and cooled to 0° C. To the cooled mixture was added DMAP (63 mg, 0.62 mmol) and 3-aminophenyl trifluoromethyl sulfone (116 mg, 0.515 mmol). The mixture was allowed to warm to room temperature and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and purified to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.31 (br s, 1H), 8.51 (s, 1H), 8.04 (m, 1H), 7.75 (d, J=5.1 Hz, 2H), 7.28 (m, 1H), 7.19 (m, 3H), 3.75 (s, 2H, CH2), 3.62 (s, 2H, CH2). MS 401.9 [M++1].

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. custompurified

Sources & evidence

ORD record
ord-f2d76b5aeb89496db5757aee01cad1a3
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06596772B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes