Triphosgene → HCID 85823632, compound

HRID 1272049Notes

Reaction equation

HRID 1272049 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:1]1([N:6]([CH2:7][C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[C:14]([Cl:13])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 961396N-(thiophen-2-ylmethyl)cyclopentanamine

Product 1

HCID 85823632HCID 85823632, compoundYield 147.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.0 g (27.58 mmol) of cyclopentylthiophen-2-ylmethylamine in 40 ml of methylene chloride at 10° C. was added slowly with stirring 4.09 g (13.79 mmol) of triphosgene in 35 ml of methylene chloride. The reaction was allowed to continue stirring at room temperature for 64 hours, refluxed for 4 hours and 25 hours more at room temperature. The solvent was evaporated and the residue extracted with n-hexane. The organic solution was concentrated to yield 4.96 g (20.34 mmol) of a brown oil (74%).

Workup

  1. temperaturerefluxed for 4 hours and 25 hours more at room temperature
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with n-hexane
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-cd0aaa2be04f442b8b5e71311999f4b6
Source dataset
uspto-grants-2007_04
Patent number
US07208501B2

Reaction notes

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