Hydrochloric Acid → HCID 68538325, compound

HRID 1991092Notes

Reaction equation

HRID 1991092 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([Cl:11])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.ClC(Cl)(O[C:23](=[O:29])OC(Cl)(Cl)Cl)Cl.C[O:32][C:33](=O)[C:34]([NH2:37])([CH3:36])[CH3:35].Cl>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([Cl:11])=[CH:5][C:3]=1[N:4]1[C:33](=[O:32])[C:34]([CH3:36])([CH3:35])[NH:37][C:23]1=[O:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 94429TriphosgeneHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 451567062-Bromo-5-chloro-4-methoxybenzenamine

Product 1

HCID 68538325HCID 68538325, compoundYield 118%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 0.60 g (2.54 mmol) 2-bromo-5-chloro-4-methoxy aniline and 0.88 ml (6.35 mmol) triethylamine in 20 ml chloroform was added 0.30 g (1.0 mmol) triphosgene at room temperature. The reaction mixture was stirred for 5 hours at r.t., then 0.47 g (3.0 mmol) 2-Amino-2-methyl-propionic acid methyl ester×HCl was added and the mixture was stirred at 60° C. overnight. The reaction was quenched with NaHCO3 solution, extracted into ethyl acetate. The organic phase was dried, evaporated and the product was purified by RP-HPLC to give 0.41 g (47%) of the desired hydantoin.

Workup

  1. stirringthe mixture was stirred at 60° C. overnight
  2. customThe reaction was quenched with NaHCO3 solution
  3. extractionextracted into ethyl acetate
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe product was purified by RP-HPLC

Sources & evidence

ORD record
ord-da2490bde8cf460ba95af4542182a852
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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