Hydrochloric Acid → HCID 86733757, compound

HRID 918411Notes

Reaction equation

HRID 918411 reaction equation
[Cl:1][CH2:2][C:3](=[O:30])[C@:4]1([OH:29])[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[O:24][CH2:25][C:26](=[O:28])[CH3:27].[Cl-:31].[Li+].ClN1C(=O)CCC1=O.[ClH:41]>C(O)(=O)C.O1CCCC1.O>[Cl:31][C@:18]12[C@@H:19]([Cl:41])[CH2:20][C@@:21]3([CH3:22])[C@@H:7]([CH2:6][C@@H:5]([O:24][CH2:25][C:26](=[O:28])[CH3:27])[C@:4]3([OH:29])[C:3](=[O:30])[CH2:2][Cl:1])[C@@H:8]1[CH2:9][CH2:10][C:11]1[C@:16]2([CH3:17])[CH:15]=[CH:14][C:13](=[O:23])[CH:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 433294Lithium ChlorideHCID 86733756HCID 86733756, compound

Product 1

HCID 86733757HCID 86733757, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21-chloro-17-hydroxy-16α-(2-oxopropoxy)pregna-1,4,9(11)-triene-3,20-dione (4mmoles) and 7.2 g of lithium chloride in 72 ml of glacial acetic acid is stirred at 0°-5°C and 592 mg of N-chlorosuccinimide is added. A solution of 180 mg of dry hydrogen chloride in 2.9 ml of tetrahydrofuran is added and the resulting mixture stirred at room temperature for 2 hours, poured into 400 ml of cold water, and extracted with chloroform. The chloroform solution is washed with water, dried, and evaporated to give the title compound.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-73b22e193ac94ab7991c1946f13e7f02
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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