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Potassium Carbonate → 9-cyano-N-(2,4-dichlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 1949891
Notes
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Reaction equation

HRID 1949891 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:15][CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([C:16]([OH:18])=O)[S:9][C:8]=3[C:7]=2[CH:19]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[Cl:26][C:27]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=1[NH:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C=O)C.C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:15][CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([C:16]([N:29]([C:28]4[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:27]=4[Cl:26])[CH3:30])=[O:18])[S:9][C:8]=3[C:7]=2[CH:19]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 28009352,4-Dichloro-N-methylanilineHCID 568341569-Cyano-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid

Product 1

HCID 579002529-cyano-N-(2,4-dichlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-cyano-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid (300 mg) in dichloromethane (10 mL) was added DMF (1 drop) and oxalyl chloride (0.165 mL) and the reaction stirred at room temperature for 30 min. The solvent was then reduced in vacuo and the residue redissolved in acetonitrile (10 mL). To this solution was added 2,4-dichloro-N-methylaniline (0.16 mL) and potassium carbonate (308 mg) and the reaction stirred at room temperature for 16 h. The mixture was partitioned between water (40 mL) and ethyl acetate (30 mL). The organic layer was dried (Na2SO4), reduced in vacuo and purified on silica to give 336. (CDCl3): 3.11 (2H, t), 3.39 (3H, s), 4.32 (2H, t), 6.91 (1H, s), 7.07 (1H, d), 7.32 (1H, d), 7.37-7.44 (2H, m), 7.58 (1H, s), 7.79 (1H, s). MH+ 429:431:433 (3:2:1)

Workup

  1. stirringthe reaction stirred at room temperature for 16 h
  2. customThe mixture was partitioned between water (40 mL) and ethyl acetate (30 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. custompurified on silica

Sources & evidence

ORD record
ord-8c1853d099954350bb59f9fa61489c8c
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399690B2

Reaction notes

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