Hydrochloric Acid → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamate

HRID 856188Notes

Reaction equation

HRID 856188 reaction equation
N1C=CC=CC=1.ClC(Cl)(O[C:11](=[O:17])[O:12][C:13](Cl)(Cl)Cl)Cl.OC[C@:21]1([CH3:32])[O:25][C:24]2=[N:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][N:23]2[CH2:22]1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)=[CH:36][CH:35]=1.Cl>C(Cl)Cl>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[C:11](=[O:17])[O:12][CH2:13][C@:21]2([CH3:32])[O:25][C:24]3=[N:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][N:23]3[CH2:22]2)=[CH:36][CH:35]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 94429TriphosgeneHCID 234111Bis(p-chlorophenyl)amineHCID 26596862(r)-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanol

Product 1

HCID 69481080(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamateYield 35.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.37 ml, 4.5 mmol) and triphosgene (0.16 g, 0.5 mmol) were added to a suspension of (R)-2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 37 (0.30 g, 1.5 mmol) in methylene chloride (15 ml) with cooling on ice-bath followed by stirring at room temperature for 2.5 hours. To the reaction mixture, bis(4-chlorophenyl)amine (0.39 g, 1.6 mmol) was added, and the resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was cooled on ice-bath and added 10% hydrochloric acid. The resulting mixture was extracted with methylene chloride, and the extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silicagel column chromatography (methylene chloride/ethyl acetate=19/1) and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamate (82 mg, yield 12%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringthe resulting mixture was stirred at room temperature for 20 hours
  3. temperatureThe reaction mixture was cooled on ice-bath
  4. extractionThe resulting mixture was extracted with methylene chloride
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silicagel column chromatography (methylene chloride/ethyl acetate=19/1)
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-83cb12cfe28846a3b2a4a03eca321d87
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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