Butyl bromide → HCID 13709807, compound

HRID 267475Notes

Reaction equation

HRID 267475 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3]1.[CH2:13](Br)[CH2:14][CH2:15][CH3:16]>CCOCC>[CH2:13]([N:3]1[C:2]([CH3:12])([CH3:1])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]1([CH3:11])[CH3:10])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 21394477HCID 21394477, compound

Product 1

HCID 13709807HCID 13709807, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

38.2 g (0.2 mole) of 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is heated with 13.7 g of n-butylbromide for 120 hours at 95°-100°C. After cooling, the contents of the flask are taken up in 300 ml of ether. The difficulty soluble hydrobromide of 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is separated by filtration, and the ether solution extracted twice with 100 ml of water each time, in order to remove the last traces of starting product or its hydrobromide. The ether solution is dried over sodium sulphate and then fully concentrated by evaporation. The residue is crystallised from ligroin to obtain 1-butyl-2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide, M.P. 180°C (3).

Workup

  1. temperatureAfter cooling
  2. customThe difficulty soluble hydrobromide of 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is separated by filtration
  3. extractionthe ether solution extracted twice with 100 ml of water each time
  4. customin order to remove the last traces of starting product or its hydrobromide
  5. dry with materialThe ether solution is dried over sodium sulphate
  6. concentrationfully concentrated by evaporation
  7. customThe residue is crystallised from ligroin

Sources & evidence

ORD record
ord-65af064147474c8386443b9990ffa4e2
Source dataset
uspto-grants-1976_03
Patent number
US03943098

Reaction notes

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