Triethylamine → HCID 66817088, compound

HRID 1754972Notes

Reaction equation

HRID 1754972 reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[NH2:13][C:14]([CH3:27])([CH3:26])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[C:20]([CH3:25])[CH:19]=1)=[O:16].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([N:17]2[C:15](=[O:16])[C:14]([CH3:26])([CH3:27])[NH:13][C:1]2=[O:12])=[CH:19][C:20]=1[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 94429TriphosgeneHCID 28263930HCID 28263930, compound

Product 1

HCID 66817088HCID 66817088, compoundYield 287.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(trichloromethyl) carbonate (50.6 mg, 0.171 mmol) was added to a solution of 2-amino-N-(4-bromo-3-methyl-phenyl)-2-methyl-propionamide (132 mg, 0.487 mmol) and triethylamine (0.204 ml, 1.46 mmol) in dichloromethane (5.0 ml) at 0° C., and the mixture was stirred for 21 hours while gradually warming to room temperature. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with dichloromethane. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give 3-(4-bromo-3-methyl-phenyl)-5,5-dimethyl-imidazolidine-2,4-dione (146 mg, 88%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-5e0f44def08e418a91a2b0829a800254
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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