Benzene → 2,2-Dichloro-1-(1-thia-4-azaspiro[4.5]decan-4-yl)ethan-1-one

HRID 127483Notes

Reaction equation

HRID 127483 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:8][CH2:9][CH2:10][NH2:11].C1C=CC=CC=1.[Cl:18][CH:19]([Cl:23])[C:20](Cl)=[O:21]>O>[Cl:18][CH:19]([Cl:23])[C:20]([N:11]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[S:8][CH2:9][CH2:10]1)=[O:21]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6058CysteamineHCID 6593Dichloroacetyl chlorideHCID 7967Cyclohexanone

Product 1

HCID 132772032,2-Dichloro-1-(1-thia-4-azaspiro[4.5]decan-4-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

From a boiling mixture of 9.8 g. (0.1 moles) of cyclohexanone and 7.7 g. (0.1 moles) 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 11 g. of a 40% aqueous sodium hydroxide solution are added followed by dropwise addition of 14.7 g. (0.1 moles) of dichloroacetyl chloride, with external salt/ice cooling. Mixture is stirred for a further two hours at room temperature and washed with aqueous hydrochloric acid solution and subsequently with water. From the neutral mixture obtained benzene is distilled off in vacuo to give 17.2 g. (0.064 moles) of a white powder. Recrystallization from absolute ethanol yields a white crystalline product melting at 149° to 151° C. The structure of the named compound can be verified by IR spectrum analysis.

Workup

  1. additionFrom a boiling mixture of 9.8 g
  2. distillationis continuously distilled off
  3. customof water are separated
  4. temperatureThe reaction mixture is then cooled
  5. additionof a 40% aqueous sodium hydroxide solution are added
  6. additionfollowed by dropwise addition of 14.7 g
  7. washwashed with aqueous hydrochloric acid solution and subsequently with water
  8. customFrom the neutral mixture obtained benzene
  9. distillationis distilled off in vacuo
  10. customto give 17.2 g
  11. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-c9ccf6a9241a4f148b83292be52195c3
Source dataset
uspto-grants-1981_03
Patent number
US04256481

Reaction notes

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