Phosgene → 1-(3-Isocyanatophenyl)-3,3-dimethylpyrrolidine-2,5-dione

HRID 435045Notes

Reaction equation

HRID 435045 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][C:10]([CH3:15])([CH3:14])[C:9]2=[O:16])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:24](Cl)(Cl)=[O:25]>O1CCCC1>[N:1]([C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][C:10]([CH3:14])([CH3:15])[C:9]2=[O:16])[CH:5]=[CH:6][CH:7]=1)=[C:24]=[O:25]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 13189216N-m-AMINOPHENYL-2,2-DIMETHYLSUCCINIMIDE

Product 1

HCID 131892331-(3-Isocyanatophenyl)-3,3-dimethylpyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Seventy-three g. of N-m-aminophenyl-2,2-dimethylsuccinimide, as prepared in Example II, was dissolved in 800 ml. of tetrahydrofuran containing 75 g. of triethylamine, cooled in an ice bath, and added to 60 g. of phosgene in 400 ml. of tetrahydrofuran maintained at about 0° C. in a drying and isopropanol bath. The mixture was allowed to warm to room temperature and the triethylamine hydrochloride was filtered off and the tetrahydrofuran removed under vacuum on the rotary evaporator. Yield was 84 g. of material product having a nD30 of 1.5470. The product was identified as the title compound by analysis of infrared spectra and was used without further purification.

Workup

  1. dissolutionwas dissolved in 800 ml
  2. additionadded to 60 g
  3. filtrationthe triethylamine hydrochloride was filtered off
  4. customthe tetrahydrofuran removed under vacuum on the rotary evaporator
  5. customwas used without further purification

Sources & evidence

ORD record
ord-acb00831fb814ab2865cb0448d305d2c
Source dataset
uspto-grants-1983_08
Patent number
US04400202

Reaction notes

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