1,2-Dichloroethane → HCID 70972224、化合物

HRID 2409914ノート

反応式

HRID 2409914 の反応式
[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9](O)=[O:10])=[CH:4][N:3]=[CH:2]1.Cl.CN.C(Cl)CCl.C1C=[N:26][C:25]2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CCOC(C)=O.CO.CN(C=O)C>[CH3:25][NH:26][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([C:5]2[O:1][CH:2]=[N:3][CH:4]=2)[CH:7]=1

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6364545Methylamine hydrochlorideHCID 71278133-(1,3-oxazol-5-yl)benzoic Acid

生成物 1

HCID 70972224HCID 70972224、化合物収率 48%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

DMF (15.9 mL) was added to a round bottom flask containing 3-(oxazol-5-yl)benzoic acid (0.99 gm, 5.23 mmol), methylamine hydrochloride (0.39 gm, 5.76 mmol), EDC (1.10 gm, 5.76 mmol), and HOAt (0.78 gm, 5.76 mmol). DIPEA (2.29 mL, 13.08 mmol) was then added. The reaction mixture was stirred at rt overnight. After 24 h the mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes then 15% MeOH in EtOAc to give the product, N-methyl-3-(oxazol-5-yl)benzamide, (0.50 gm, 2.49 mmol, 48% yield) as a white solid. Anal. Calcd. for C11H10N2O2 m/z 202.1, found: 203.1 (M+H)+.

後処理

  1. customAfter 24 h the mixture was partitioned between EtOAc and water
  2. customThe organic phase was isolated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified
  8. washeluting with a gradient of 0-100% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-dfe440ed1c464e049ded24fa8671699f
出典データセット
uspto-grants-2014_08
特許番号
US08815909B2

反応ノート

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