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1,1'-Carbonyldiimidazole → 5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetamide

HRID 1899079
Notes
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Reaction equation

HRID 1899079 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14](O)=[O:15])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:29]1C=CN=C1)=O.O.N>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14]([NH2:29])=[O:15])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 117947425-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetic acidHCID 12896473Azane;hydrate

Product 1

HCID 233727565-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetamideYield 78.2%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetic acid (4.1 g) and 1,1'-carbonyldiimidazole (1.8 g) in tetrahydrofuran (50 ml) was stirred and refluxed for 1 hour. The mixture was added dropwise to an ice-cooled mixture of ammonia water (28%; 5 ml) and tetrahydrofuran (10 ml). The resulting mixture was stirred overnight, diluted with water, and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate, water, and dilute hydrochloric acid, successively. The organic layer was dried and concentrated, and the residue was recrystallized from a mixture of chloroform, ethyl acetate and ethanol to give crystals of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetamide (3.2 g).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperaturecooled
  3. stirringThe resulting mixture was stirred overnight
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium bicarbonate, water, and dilute hydrochloric acid
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customthe residue was recrystallized from a mixture of chloroform, ethyl acetate and ethanol

Sources & evidence

ORD record
ord-1a409b6469864cf28d5d9634197eee70
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05571810

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes