Triphosgene → Butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride

HRID 1760829Notes

Reaction equation

HRID 1760829 reaction equation
[CH2:1]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH3:4].[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:1]([N:5]([C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:19])[C:8]=2[CH:7]=1)[C:21]([Cl:20])=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 22596841Butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine

Product 1

HCID 22596833Butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chlorideYield 595.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (7) (143 mg, 0.55 mmole) in 20 mL of THF was treated with 57 mg of triphosgene (0.35 eq.), stirred at reflux for three hours and then poured onto 50 mL ice-water. The mixture was extracted with three portions of 50 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to provide 368 mg of butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride (9) which was used without purification.

Workup

  1. temperatureat reflux for three hours
  2. extractionThe mixture was extracted with three portions of 50 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-162411f954a44a2cb2b42acfbfcbde5f
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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