Sodium hydride → HCID 68148414, compound

HRID 1606300Notes

Reaction equation

HRID 1606300 reaction equation
[OH:1][C:2]1[C:19]2[C@@H:18]3[C@@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.[H-].[Na+].[CH2:24]([N:26]([CH2:31][CH3:32])[S:27](Cl)(=[O:29])=[O:28])[CH3:25]>CS(C)=O>[CH2:24]([N:26]([CH2:31][CH3:32])[S:27]([O:1][C:2]1[C:19]2[C@@H:18]3[C@@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][S:27]([N:26]([CH2:31][CH3:32])[CH2:24][CH3:25])(=[O:29])=[O:28])[CH:3]=1)(=[O:29])=[O:28])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11252267N,N-diethylsulfamoyl chlorideHCID 68148298HCID 68148298, compound

Product 1

HCID 68148414HCID 68148414, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 250 mg. of 1,3-dihydroxy-8α-estra-1,3,5(10)-trien-17-one in 6.5 ml. of dimethyl sulfoxide is mixed under cooling and nitrogen with 250 mg. of NaH (50% suspension in oil), and agitated for 30 minutes at room temperature. A solution of 1.05 g. of diethylaminosulfonyl chloride in 2 ml. of dimethyl sulfoxide is then added to the mixture, and the latter is agitated for 25 hours at room temperature. The mixture is introduced into acetic ice water (NaCl), the organic substances are extracted with ether, and the extracts are washed, dried, and evaporated. After purificationby chromatography, 150 mg. of 1,3-bis(diethylaminosulfonyloxy)-8α-estra-1,3,5(10)-trien-17-one is produced.

Workup

  1. temperatureunder cooling
  2. extractionthe organic substances are extracted with ether
  3. washthe extracts are washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9e77b6ae96a14f8296bba07eff90a358
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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