Pyridine → 2,2-Dichloro-1-(1-thia-4-azaspiro[4.4]nonan-4-yl)ethan-1-one

HRID 127486Notes

Reaction equation

HRID 127486 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:7][CH2:8][CH2:9][NH2:10].N1C=CC=CC=1.[Cl:17][CH:18]([Cl:22])[C:19](Cl)=[O:20]>O.C1C=CC=CC=1>[Cl:17][CH:18]([Cl:22])[C:19]([N:10]1[C:1]2([CH2:5][CH2:4][CH2:3][CH2:2]2)[S:7][CH2:8][CH2:9]1)=[O:20]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6058CysteamineHCID 6593Dichloroacetyl chlorideHCID 8452Cyclopentanone

Product 1

HCID 132882242,2-Dichloro-1-(1-thia-4-azaspiro[4.4]nonan-4-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

From a boiling mixture of 8.4 g. (0.1 moles) of cyclopentanone and 7.7 g. (0.1 mole) of 2-mercaptoethylamine in 100 ml. of benzene the water formed is continuously distilled off. Boiling is continued until 1.8 ml. of water are separated. The reaction mixture is then cooled and 8 g. (0.1 moles) of pyridine are added followed by a dropwise addition of 14.7 g. (0.1 moles) of dichloroacetyl chloride, with external salt/ice cooling.

Workup

  1. additionFrom a boiling mixture of 8.4 g
  2. distillationis continuously distilled off
  3. customof water are separated
  4. temperatureThe reaction mixture is then cooled
  5. additionfollowed by a dropwise addition of 14.7 g

Sources & evidence

ORD record
ord-a2484bc604cd45888f4374b7991a520c
Source dataset
uspto-grants-1981_03
Patent number
US04256481

Reaction notes

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