1-Bromo-1-chloroethane → 3-(2-Chloroethyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

HRID 1023490

Reaction equation

HRID 1023490 reaction equation
[CH3:1][C:2]1([CH3:16])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:4]2([NH:8][C:7](=[O:9])[NH:6][C:5]2=[O:10])[CH2:3]1.[OH-].[K+].Br[CH:20]([Cl:22])[CH3:21]>CCO>[Cl:22][CH2:20][CH2:21][N:6]1[C:5](=[O:10])[C:4]2([CH2:3][C:2]([CH3:16])([CH3:1])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11]2)[NH:8][C:7]1=[O:9]

Participants

5

Reactant 3

HCID 116541-Bromo-1-chloroethaneHCID 14797Potassium HydroxideHCID 12680667,7,9,9-Tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 593551913-(2-Chloroethyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (5, 22.2 mmol) and KOH (1.24 g, 22.2 mmol) in EtOH was refluxed for 10 min and bromochloroethane (6.35 g, 44.4 mmol) was added and refluxing continued for additional 6 h. Filtered and concentrated to get the crude chloroethylated product which was used as such for the next step (5.5 g). LCMS—[M+H] m/z 228.

Workup

  1. temperaturewas refluxed for 10 min
  2. temperaturerefluxing
  3. filtrationFiltered
  4. concentrationconcentrated
  5. customto get the crude chloroethylated product which

Sources & evidence

ORD record
ord-fd171ac22d1b464b8671e2f36b6dd81c
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Linked notes

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