Ammonium Chloride → HCID 20328821, compound

HRID 372234

Reaction equation

HRID 372234 reaction equation
[Mg].Cl[CH:3]1[CH2:12][N:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4]1.[Cl:13][C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:28])[C:16]=2[CH:15]=1.[Cl-].[NH4+]>C(Br)C.O1CCCC1>[Cl:13][C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:3]3[CH2:12][N:11]4[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]4)[CH2:5][CH2:4]3)([OH:28])[C:16]=2[CH:15]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6188482-ChlorothioxanthoneHCID 5462224MagnesiumHCID 203288343-Chloroquinolizidine

Product 1

HCID 20328821HCID 20328821, compound

Reagents, catalysts & solvents 2

HCID 6332Ethyl BromideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Several drops of ethyl bromide were added to a stirred suspension of 1.29 g. (0.054 g.-atom) of magnesium turnings in 5 ml. of tetrahydrofuran under a nitrogen atmosphere. After the reaction began 9.3 g. (0.054 mole) of 3-chloroquinolizidine in 100 ml. of tetrahydrofuran was added. After the addition was completed the mixture was stirred and refluxed for one hour and cooled to 0° C. To the chilled suspension of the Grignard reagent was added a solution of 12.55 g. (0.051 mole) of 2-chloro-9-thioxanthone in 300 ml. of tetrahydrofuran. The solution was stirred at 24° C. for two hours, poured into aqueous ammonium chloride and extracted with ether. The extracts were washed with water, dried and evaporated to give 2-chloro-9-(3-quinolizidinyl)-9-hydroxythioxanthene.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for one hour
  3. additionwas added a solution of 12.55 g
  4. stirringThe solution was stirred at 24° C. for two hours
  5. extractionextracted with ether
  6. washThe extracts were washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-7e97f4f7917a405781fe469772573c1d
Source dataset
uspto-grants-1978_05
Patent number
US04089961

Linked notes

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