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Triethylamine → Methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate

HRID 322058
Notes
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Reaction equation

HRID 322058 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[N:13][OH:14])=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].ClN1C(=O)CCC1=O.[CH2:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:28]=[CH2:29].C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[C:11]([C:12]2[CH2:29][CH:28]([CH2:27][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:14][N:13]=2)=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9309AllylbenzeneHCID 31398ChlorosuccinimideHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 22009884Methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

0.80 g (2.7 mmol) of methyl 2-chloro-3-hydroximinomethyl-4-methylsulfonylbenzoate are dissolved in 20 ml of dimethylformamide with 0.38 g (2.9 mmol) of N-chlorosuccinimide. After stirring at room temperature for 4 hours, 0.49 g (2.9 mmol) of allylbenzene and then 0.29 g (2.9 mmol) of triethylamine are added dropwise at 0° C. After stirring at room temperature for 16 hours, the reaction mixture is concentrated in a rotary evaporator, the residue is dissolved in dichloromethane and the solution is washed with sodium bicarbonate solution and with water. After drying over magnesium sulfate and evaporating the solvent, 1.1 g (100% of theory) of methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate are obtained as a colorless oil.

Workup

  1. stirringAfter stirring at room temperature for 16 hours
  2. concentrationthe reaction mixture is concentrated in a rotary evaporator
  3. dissolutionthe residue is dissolved in dichloromethane
  4. washthe solution is washed with sodium bicarbonate solution and with water
  5. dry with materialAfter drying over magnesium sulfate
  6. customevaporating the solvent, 1.1 g (100% of theory) of methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate
  7. customare obtained as a colorless oil

Sources & evidence

ORD record
ord-6bbc9bcc916c492099d69602d99cbf53
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211216B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes