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Hydrochloric Acid → 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide

HRID 17605
ノート
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反応式

HRID 17605 の反応式
C[Al](C)C.CCCCCC.Cl.[CH3:12][NH:13][CH3:14].[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([O:32]C)=O)=[C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:18]=1[CH3:40])#[N:16].Cl>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:27][CH2:28]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([N:13]([CH3:14])[CH3:12])=[O:32])=[C:19]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:18]=1[CH3:40])#[N:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 86584505Trimethylaluminum hexaneHCID 86630881Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

生成物 1

HCID 685875632-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide収率 83%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

At room temperature, trimethylaluminium/n-hexane solution (1.03 mol/l) (547 μl, 0.563 mmol) was added to a toluene (2 ml) suspension of dimethylamine hydrochloride (38.3 mg, 0.469 mmol), followed by stirring at room temperature for 30 minutes. Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate (I-295) (65.0 mg, 0.188 mmol) was added to the reaction liquid, followed by heating under reflux in an oil bath at 120° C. for 15 hours. With cooling with ice, 1 N hydrochloric acid was added to the reaction liquid. After extraction with ethyl acetate, the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (56.0 mg, 83%) as a white solid.

後処理

  1. temperatureby heating
  2. temperatureunder reflux in an oil bath at 120° C. for 15 hours
  3. additionwas added to the reaction liquid
  4. extractionAfter extraction with ethyl acetate
  5. washthe obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe insoluble matter was separated by filtration
  8. customthe residue obtained by concentration
  9. customwas purified by preparative TLC (eluent, chloroform

出典と根拠

ORDレコード
ord-c2b027ba9ea2410a96e4cf33a7a633b3
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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