p-Bromobenzenesulfonyl chloride → HCID 57282319, compound

HRID 1078970Notes

Reaction equation

HRID 1078970 reaction equation
[OH:1][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[CH3:24].O1CCCC1.C(N(CC)CC)C.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>O>[Br:38][C:39]1[CH:44]=[CH:43][C:42]([S:45]([O:1][CH2:2][C:3](=[O:25])[C@@H:4]2[C@:21]3([CH3:22])[C@H:7]([C@H:8]4[C:18](=[CH:19][CH2:20]3)[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]3)[CH2:10][CH2:9]4)[CH2:6][C@H:5]2[CH3:24])(=[O:47])=[O:46])=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1458523921-Hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

Product 1

HCID 57282319HCID 57282319, compoundYield 67.07%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing 10.0 g (29.4 moles) of 21-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione in 100 mol of tetrahydrofuran, first 7,14 ml (51.4 mmoles) of triethylamine, then at 0° C. 13.1 g (51.4 moles) of 4-bromobenzenesulfonyl chloride are added, the reaction mixture is stirred at room temperature for 4 hours, then it is dropwise added to 450 ml of water while stirring. The precipitate is filtered off, dried and recrystallized from ether to obtain 11.0 g (67.07%) of the title compound, m.p.: 124°-129° C.

Workup

  1. customat 0° C
  2. stirringwhile stirring
  3. filtrationThe precipitate is filtered off
  4. customdried
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-a2b276ca76e24203b3e38a4925daf82a
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

Loading…