Sodium ethoxide → HCID 19087825, compound

HRID 1464345Notes

Reaction equation

HRID 1464345 reaction equation
C(S[C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:12](=[O:51])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)C.[O-:52][CH2:53][CH3:54].[Na+]>C(O)C>[CH2:53]([O:52][C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:12](=[O:51])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:54]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 19087815HCID 19087815, compound

Product 1

HCID 19087825HCID 19087825, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-ethylthio-3-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-4(3H)-quinazolinone (0.5 g) and sodium ethoxide (182 mg) in ethanol (20 ml) was stirred at room temperature for 3 days. The reaction mixture was concentrated to dryness. The residue was extracted using methylene chloride and an aqueous solution of ammonium chloride. The organic layer was washed with water, dried and evaporated to dryness. The resulting syrup was purified by column chromatography on silica gel to give a colorless oil (72 mg, 21%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionThe residue was extracted
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe resulting syrup was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c375773723d24fb2912984a491d25d55
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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