Water → HCID 70239941, compound

HRID 1351453Notes

Reaction equation

HRID 1351453 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([CH2:25][C:26]#[N:27])(=[O:24])=[O:23].N1CCCCC1.O>C(O)C>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:25]([S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)(=[O:24])=[O:23])[C:26]#[N:27])[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 5193552-Pyridinesulfonylacetonitrile

Product 1

HCID 70239941HCID 70239941, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 450 mg (2.2 mmole) of 3,5-diisopropy-4-hydroxylbenzaldehyde and 400 mg (2.2 mmole) of 2-pyridinesulfonlyacetonitrile (Lancaster catalog number 7114) in 10 ml of ethanol was refluxed with few drop of piperidine for 3 hours. The reaction was then cooled to room temperature and added with about 5 ml of water until crystallization began. After standing at 0° C. for 2 hours, all the solid was collected and dried by suction filtration to provide 350 mg M26 (0.95 mmole, 43% yield) as an orange solid. The purity of this material is over 95% by HPLC and the structure confirmed by NMR, MS and IR.

Workup

  1. customall the solid was collected
  2. customdried by suction filtration
  3. customto provide 350 mg M26 (0.95 mmole, 43% yield) as an orange solid

Sources & evidence

ORD record
ord-d2b2bd1edf5a4bf1b776b4b59053731b
Source dataset
uspto-grants-2007_05
Patent number
US07217737B2

Reaction notes

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