Sodium hydride → HCID 21846483, compound

HRID 725211Notes

Reaction equation

HRID 725211 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: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[CH2:22][CH2:6][CH2:7][OH:21]

Participants

4

Reactant 2

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

Product 1

HCID 21846483HCID 21846483, compoundYield 147.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Using the procedure of Example 4, 109 mg of 50% sodium hydride, 510 mg of the product of Example 2 and 4 ml of dimethylsulfoxide were reacted and rinsing was carried out with 0.5 ml of dimethylsulfoxide. Then, 20 minutes after the release of hydrogen had stopped, 1.004 g of 3-bromopropoxydiphenyl-tert-butyl-silane were added and the solution was heated to about 50° C. Proceeding as in Example 4, the solution was taken up in 30 ml of methanol, 10 ml of 2N hydrochloric acid, 10 ml of chloroform and refluxed. After purification on silica with methylene chloride-acetone: 8-2 as eluant, 441 mg of the expected product (white crystals) melting at 155°-156° C. were obtained.

Workup

  1. customwere reacted
  2. washrinsing
  3. custom20 minutes
  4. addition1.004 g of 3-bromopropoxydiphenyl-tert-butyl-silane were added
  5. temperature10 ml of 2N hydrochloric acid, 10 ml of chloroform and refluxed
  6. customAfter purification on silica with methylene chloride-acetone

Sources & evidence

ORD record
ord-9f3b25bf8b50447baff336fe78562b11
Source dataset
uspto-grants-1998_01
Patent number
US05705654

Reaction notes

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