Triphosgene → HCID 11484465, compound

HRID 394923Notes

Reaction equation

HRID 394923 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>O1CCCC1>[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 279%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude oil was dissolved in 140 ml of ethanol, treated with a solution of 10 g of potassium hydroxide in 20 ml of water and stirred at room temperature for 2 hours. The reaction mixture was poured on ice water, extracted with ether, dried (Na2SO4) and the solvent evaporated. The oily residue was filtered through silica gel (eluent hexane/10% ethyl acetate) to give 9.8 g of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine as a slightly yellow oil. A solution of 1 g of this amine in 20 ml of tetrahydrofuran was treated with 380 mg of triphosgene, heated to reflux for 3 hours, then poured on ice water and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and the solvent evaporated. The oily residue was crystallized in pentane to give 1.2 g of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride in white crystals, m.p. 79-81° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. additionpoured on ice water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customThe oily residue was crystallized in pentane

Sources & evidence

ORD record
ord-dcc7d75521ce4131b0c351f273d30620
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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