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Phosphorus oxychloride → 4-(2,4-dichlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)-2-morpholin-4-ylthiophene-3-carbonitrile

HRID 2091687
Notes
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Reaction equation

HRID 2091687 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:10]([C:20]#[N:21])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:11]1[C:10]([C:20]#[N:21])=[C:9]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[S:8][C:7]=1[C:5]1[NH:4][CH2:3][CH2:2][N:1]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67073109N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide

Product 1

HCID 685293044-(2,4-dichlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)-2-morpholin-4-ylthiophene-3-carbonitrileYield 95.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide (2.50 g, 5.90 mmol) in toluene (20 mL) was added phosphoryl chloride (4.70 mL, 50.0 mmol) and the mixture was stirred under microwave irradiation at 120° C. for 25 minutes. The reaction mixture was evaporated and the residue was suspended in methylene chloride and then quenched with ice water. The aqueous layer was basified by addition of KOH, the layers were separated and the aqueous layer was extracted again with methylene chloride. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product (2.3 gr, 77%). LCMS: (FA) ES+ 408. 1H NMR (400 MHz, d6-DMSO) δ: 7.78-7.75 (m, 1H), 7.52-7.49 (m, 2H), 3.79-3.73 (m, 4H), 3.63-3.55 (m, 2H), 3.54-3.48 (m, 4H), 3.20-3.11 (m, 2H).

Workup

  1. customThe reaction mixture was evaporated
  2. customquenched with ice water
  3. additionThe aqueous layer was basified by addition of KOH
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted again with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a65bfd1fdc4d4d1193a588c257941aeb
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440664B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes