Sodium hydride → HCID 21846471, compound

HRID 264017Notes

Reaction equation

HRID 264017 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][S: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][S:24][CH2:23][CH2:22]2)[N:5]1[CH2:23][CH2:22][CH2:6][CH2:7][OH:21]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21846482HCID 21846482, compound

Product 1

HCID 21846471HCID 21846471, compoundYield 148.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using the procedure of Example 3, 55 mg of 50% sodium hydride and 355 mg of the product of Example 13 were reacted and 2.5 ml of dimethylsulfoxide were added dropwise over 20 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-iodo-butoxy-trimethylsilane were added. The reaction medium was poured into 25 ml of water containing 0.1 g of monopotassium phosphate and extraction was carried out 3 times with ether. The organic phase was washed with water, then with salt water and dried. The resultant product was taken up in 10 ml of methanol and 1 ml of 2N hydrochloric acid and left for 30 minutes. It was poured into 30 ml of 50% sodium chloride and extraction was carried out 3 times with ethyl acetate. The extracts were washed with salt water and dried. Purification was carried out on silica with methylene chloride-acetone: 9-1 as eluant to obtain 317 mg of the expected product (white crystals) melting at 139°-140° C.

Workup

  1. customwere reacted
  2. washRinsing
  3. customwas carried out with 0.5 ml of dimethylsulfoxide and 20 minutes
  4. addition0.41 g of 4-iodo-butoxy-trimethylsilane were added
  5. additionThe reaction medium was poured into 25 ml of water containing 0.1 g of monopotassium phosphate and extraction
  6. washThe organic phase was washed with water
  7. dry with materialwith salt water and dried
  8. additionIt was poured into 30 ml of 50% sodium chloride and extraction
  9. washThe extracts were washed with salt water
  10. customdried
  11. customPurification

Sources & evidence

ORD record
ord-2b8993286c354c69a945e9c91ec1fe9b
Source dataset
uspto-grants-1997_07
Patent number
US05646172

Reaction notes

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