Acetone → HCID 12961967, compound

HRID 1065701Notes

Reaction equation

HRID 1065701 reaction equation
Cl.[Cl:2][C@:3]12[CH2:20][C@@H:19]([OH:21])[CH2:18][CH2:17][C@:16]1([CH3:22])[C@@H:15]1[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C@@H:10]([NH:23][CH3:24])[C@H:9]([OH:25])[CH2:8]3)[CH2:5][C@H:4]2[Cl:26].CC(C)=O>CO.C(Cl)(Cl)Cl>[ClH:2].[Cl:2][C@:3]12[CH2:20][C@@H:19]([OH:21])[CH2:18][CH2:17][C@:16]1([CH3:22])[C@@H:15]1[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C@@H:10]([NH:23][CH3:24])[C@H:9]([OH:25])[CH2:8]3)[CH2:5][C@H:4]2[Cl:26]

Participants

6

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 12961966HCID 12961966, compound

Product 1

HCID 12961967HCID 12961967, compoundYield 190.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Hydrogen chloride gas has passed through a solution of 5α,6β-dichloro-17β-methylamino-5α-androstane-3β,16α-diol (7.2 g) in methanol (15 ml) and chloroform (72 ml), giving a colourless precipitate. Evaporation of the solvent gave a colourless residue which was heated with acetone, filtered, and dried in vacuo to give 5α,6β-dichloro-17β-methylamino-5α-androstane-3β,16α-diol hydrochloride as prisms (7.5 g), m.p.>210° C. (decomp.), [α]D -57.1° (c 1.1 in EtOH).

Workup

  1. customgiving a colourless precipitate
  2. customEvaporation of the solvent
  3. customgave a colourless residue which
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-975da84f322f4011b31de46a56a5f116
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

Loading…