Water → (1,4-Dioxa-spiro[4.5]dec-8-yl)-carbamoyl chloride

HRID 413261Notes

Reaction equation

HRID 413261 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O.C([O-])(O)=O.[Na+].[C:18](Cl)([Cl:20])=[O:19]>C(Cl)Cl.C1(C)C=CC=CC=1>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:18]([Cl:20])=[O:19])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 146343151,4-Dioxaspiro[4.5]decan-8-amine

Product 1

HCID 22325328(1,4-Dioxa-spiro[4.5]dec-8-yl)-carbamoyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 1,4-dioxaspiro[4.5]decan-8-amine (785 mg, 0.005 mol; see Liebigs (1990) Ann. Chem. 8:781-7) in CH2Cl2 and then add H2O (20 mL) followed by saturated NaHCO3 solution (50 mL). Add a toluene solution of phosgene (20% solution, 5 mL) to the reaction mixture and stir at room temperature for 1 hour. Dry the CH2Cl2 layer (Na2SO4) and concentrate under reduced pressure. Dissolve the resulting oil in dry toluene to produce a stock solution (˜0.2 M) of (1,4-dioxa-spiro[4.5]dec-8-yl)-carbamoyl chloride.

Workup

  1. dry with materialDry the CH2Cl2 layer (Na2SO4)
  2. concentrationconcentrate under reduced pressure
  3. dissolutionDissolve the resulting oil in dry toluene

Sources & evidence

ORD record
ord-e255d53416be4191a045e2776b51e1e4
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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