Sulfuryl chloride → HCID 15351950, compound

HRID 1978824Notes

Reaction equation

HRID 1978824 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][N:7]([CH3:37])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:34][C@@:32]3([CH3:33])[C@@H:28]([CH2:29][CH2:30][C:31]3=[O:35])[C@H:27]3[C:18]2=[C:19]2[C:24]([CH2:25][CH2:26]3)=[CH:23][C:22](=[O:36])[CH2:21][CH2:20]2)=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>ClCCl.N1C=CC=CC=1>[Cl:4][C:23]1[C:22](=[O:36])[CH2:21][CH2:20][C:19]2[C:24]=1[CH2:25][CH2:26][C@@H:27]1[C:18]=2[C@@H:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][N:7]([CH3:6])[CH3:37])=[CH:16][CH:15]=2)[CH2:34][C@@:32]2([CH3:33])[C@H:28]1[CH2:29][CH2:30][C:31]2=[O:35]

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 15351949HCID 15351949, compound

Product 1

HCID 15351950HCID 15351950, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

6 ml of sulphuryl chloride at 10% in dichloromethane is added under an inert atmosphere, at ambient temperature to a solution of 1.08 g of 11β-[4-(2-(dimethylamino)ethoxy)phenyl]-estra-4,9-diene-3,17-dione in 11 ml of pyridine and agitation is carried out for 30 minutes at approximately −36° C. The reaction medium is poured into sodium bicarbonate, followed by extraction, washing, drying and evaporating under reduced pressure until 1.84 g of crude product is obtained, which is purified by chromatography, eluting with an ethyl acetate/triethylamine mixture 80/20. 616 mg of expected pure product is obtained. (Rf AcOEt/TEA 8/2=0.35).

Workup

  1. extractionfollowed by extraction
  2. washwashing
  3. customdrying
  4. customevaporating under reduced pressure until 1.84 g of crude product
  5. customis obtained
  6. customwhich is purified by chromatography
  7. washeluting with an ethyl acetate/triethylamine mixture 80/20
  8. custom616 mg of expected pure product is obtained

Sources & evidence

ORD record
ord-6889b676106b4e9a8a0023ac051ba7f9
Source dataset
uspto-grants-2001_05
Patent number
US06239121B1

Reaction notes

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