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

HRID 856188ノート

反応式

HRID 856188 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-83cb12cfe28846a3b2a4a03eca321d87
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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