Triphosgene → HCID 11484465, compound

HRID 1760838Notes

Reaction equation

HRID 1760838 reaction equation
[CH2:1]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:21][C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:1]([N:6]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2[CH:8]=1)[C:22]([Cl:21])=[O:24])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 11208062HCID 11208062, compound

Product 1

HCID 11484465HCID 11484465, compoundYield 292.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (33) (1.0 g, 3.6 mmole) in 20 mL of THF was treated with 380 mg of triphosgene (0.35 eq.). The reaction mixture was stirred at reflux for three hours, poured onto 30 mL ice-water and extracted with three portions of 30 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 1.26 g of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride (35) as a white solid, which was used without purification.

Workup

  1. temperatureat reflux for three hours
  2. extractionextracted with three portions of 30 mL of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19fe911379794f8989a19ce623b95a1e
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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