Dimethyl Sulfoxide → HCID 15345499, compound

HRID 264013Notes

Reaction equation

HRID 264013 reaction equation
[H-].[Na+].[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[NH:5]1.CS(C)=O>O>[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:5]1[CH2:23][CH2:22][CH2:6][CH2:7][OH:21]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 153454984-(2,4-Dioxo-8-oxa-1,3-diazaspiro[4.5]decan-3-yl)-2-(trifluoromethyl)-benzonitrile

Product 1

HCID 15345499HCID 15345499, compoundYield 179%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

55 mg of 50% sodium hydride were introduced and 340 mg of the product of Example 2 and 25 ml of dimethylsulfoxide were added dropwise over 25 minutes. Rinsing was carried out with 0,5 ml of dimethylsulfoxide and 20 minutes after the release of hydrogen had stopped, 0.41 g of 4-iodobutoxy-trimethyl-silane was added. The mixture was allowed to react for 18 hours at ambient temperature and the reaction medium was then poured into 10 ml of water. Extraction was carried out 4 times with ether and the organic phase was washed with water, then with salt water, dried and taken up in a mixture of 10 ml of methanol and 1 ml of 2N hydrochloric acid. After 30 minutes, the mixture was poured into 20 ml of saturated sodium chloride solution and extraction was carried out 3 times with chloroform, followed by drying. Purification was carried out on silica with methylene chloride-acetone 8-2 as eluant to obtain 369 mg of the expected product (friable white foam).

Workup

  1. washRinsing
  2. customwas carried out with 0,5 ml of dimethylsulfoxide and 20 minutes
  3. addition0.41 g of 4-iodobutoxy-trimethyl-silane was added
  4. customto react for 18 hours at ambient temperature
  5. extractionExtraction
  6. washthe organic phase was washed with water
  7. dry with materialwith salt water, dried
  8. additiontaken up in a mixture of 10 ml of methanol and 1 ml of 2N hydrochloric acid
  9. additionthe mixture was poured into 20 ml of saturated sodium chloride solution and extraction
  10. customby drying
  11. customPurification

Sources & evidence

ORD record
ord-ec9a24a752ee43aeb2a0c46e1839cd2a
Source dataset
uspto-grants-1997_07
Patent number
US05646172

Reaction notes

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