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Water → 2-Thien-2-yl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran

HRID 485617
Notes
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Reaction equation

HRID 485617 reaction equation
[OH-].[Na+].O.[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[C:11]([NH2:25])[O:10]1.S(OC)(O[CH3:30])(=O)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)=[C:11]([NH:25][CH3:30])[O:10]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 136911642-Thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran

Product 1

HCID 136911652-Thien-2-yl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran

Reagents, catalysts & solvents 2

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

In this example about 0.36 g of solid sodium hydroxide was dissolved in a small amount of water and then added to 100 ml of methylene chloride containing 1.4 g of 2-thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran. 0.20 g of benzyltriethylammonium chloride was added and then a mixture containing 0.84 ml of dimethyl sulfate in about 5.0 ml of methylene chloride was slowly added at room temperature. The mixture was stirred at room temperature for about one hour and then washed twice with water, twice with 1N. aqueous hydrochloric acid, twice with sodium bicarbonate, dried over magnesium sulfate and then concentrated by evaporation under vacuum. The residue was then triturated in a mixture of ethyl ether and petroleum ether affording 1.4 g of the title compound.

Workup

  1. additionwas slowly added at room temperature
  2. washwashed twice with water, twice with 1N
  3. dry with materialaqueous hydrochloric acid, twice with sodium bicarbonate, dried over magnesium sulfate
  4. concentrationconcentrated by evaporation under vacuum
  5. customThe residue was then triturated in a mixture of ethyl ether and petroleum ether affording 1.4 g of the title compound

Sources & evidence

ORD record
ord-fb0b3a778d7b41f0a7b7a86c4e68deb0
Source dataset
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04537623

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes