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Ammonia → HCID 9869344, compound

HRID 2305241
Notes
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Reaction equation

HRID 2305241 reaction equation
[NH3:1].CO.[C:4]1([C:10]2[N:11]=[C:12]([C:21]3[CH:22]([CH2:27][C:28]4[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:24][CH2:25][CH:26]=3)[O:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.CCOC(C)=O>[C:4]1([C:10]2[N:11]=[C:12]([C:21]3[CH:22]([CH2:27][C:28]4[CH:29]=[C:30]([S:34]([NH2:1])(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:24][CH2:25][CH:26]=3)[O:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 18459146HCID 18459146, compound

Product 1

HCID 9869344HCID 9869344, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of 28% ammonia solution (0.7 ml) and MeOH (1.0 ml) was added a solution of crude 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-benzenesulfonyl chloride (253 mg, 0.52 mmol) in tetrahydrofuran (3 ml) at 5° C. After stirring at room temperature for 30 min, the reaction mixture was diluted with EtOAc, washed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 2:1 elution) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzenesulfonamide (41.3 mg, 17%).

Workup

  1. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 2:1 elution)

Sources & evidence

ORD record
ord-4c0e8fd2dc914cc3aba2b865edd4c852
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437146B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes