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Urea → 1-(2-Amino-4-methyl-1,3-oxazol-5-yl)ethanone

HRID 1747188
ノート
印刷プレビュー

反応式

HRID 1747188 の反応式
Br[CH:2]([C:6](=O)[CH3:7])[C:3](=[O:5])[CH3:4].[NH2:9][C:10]([NH2:12])=[O:11].C([O-])(O)=O.[Na+].[Na+].[Cl-]>CC(C)=O.O.CCOC(C)=O>[NH2:12][C:10]1[O:11][C:2]([C:3](=[O:5])[CH3:4])=[C:6]([CH3:7])[N:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1176UreaHCID 5234Sodium ChlorideHCID 3556413-Bromopentane-2,4-dioneHCID 516892Sodium Bicarbonate

生成物 1

HCID 108444531-(2-Amino-4-methyl-1,3-oxazol-5-yl)ethanone収率 57.9%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒
HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

3-Bromo-2,4-pentandione (P8) (26.66 g, 148.93 mmol) obtained in Step I as described above, is dissolved in acetone (87 mL). This mixture is added to a solution of urea (22.36 g, 372 mmol, 2.5 eq) in water (20 mL). The resulting mixture is heated in order to obtain a clear solution and is distributed into 38 microwave tubes (3 ml each). The vials are heated to 100° C. for 1200 s each in the microwave oven. All vials are combined, NaHCO3 sat (100 ml) and EtOAc (100 ml) are added, the aqueous phase is saturated with NaCl and the phases are separated. The aqueous phase is extracted with EtOAc (4 times 100 ml). Combined organic layers are dried over MgSO4, filtrated and evaporated under reduced pressure to give 1-(2-amino-4-methyl-1,3-oxazol-5-yl)ethanone (P5) as an orange solid (12.09 g). It is further recrystallized in MeOH, affording a brownish solid (5.56 g, 27%). 1H NMR (DMSO-d6) δ: 2.22 (s, 3H), 2.25 (s, 3H), 7.51 (s, 2H).

後処理

  1. temperatureThe resulting mixture is heated in order
  2. customto obtain a clear solution
  3. additionare added
  4. customthe phases are separated
  5. extractionThe aqueous phase is extracted with EtOAc (4 times 100 ml)
  6. dry with materialCombined organic layers are dried over MgSO4
  7. filtrationfiltrated
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5310dfdd1a8c4e1ea46ee75bcd165ab2
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150561B2

反応ノート

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