Phosgene → Dabco

HRID 484380Notes

Reaction equation

HRID 484380 reaction equation
C(Cl)(Cl)=O.C(Cl)(=O)OC.[C:10](Cl)(=O)O[CH2:12][CH3:13].C(Cl)(=O)OC[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:27]([C:34]1[NH:35][CH:36]=[CH:37][N:38]=1)([C:29]1[NH:30]C=CN=1)=O>C(N(CC)CC)C>[CH:34]([N:35]([CH:24]([CH3:23])[CH3:19])[CH2:36][CH3:37])([CH3:27])[CH3:10].[N:35]12[CH2:13][CH2:12][N:38]([CH2:27][CH2:34]1)[CH2:37][CH2:36]2.[N:30]12[CH2:29][CH2:27][CH2:34][N:38]=[C:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2

Participants

9

Reactant 5

HCID 6371PhosgeneHCID 6586Methyl chloroformateHCID 10387Benzyl chloroformateHCID 10928Ethyl chloroformateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 3

HCID 9237DabcoHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The compound (V) is reacted with a carbonic ester (e.g. diethyl carbonate, dimethyl carbonate, benzyl carbonate) in the presence of a base (e.g. lithium carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, diisopropylethylamine, triethylamine) to produce the compound (VI). Alternatively, the compound (V) is reacted with phosgene, methyl chlorocarbonate, ethyl chlorocarbonate, benzyl chlorocarbonate or carbonyl diimidazole or its related compound, if necessary, in the presence of a base (e.g. triethylamine, diisopropylethylamine, 1,4-di azabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]undec-7-ene) to give the compound (VI).

Sources & evidence

ORD record
ord-755d66e8515f4c249a3065dd09fd5f46
Source dataset
uspto-grants-1993_07
Patent number
US05231179

Reaction notes

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