1,2-Dichloroethane → HCID 70972224, 화합물

HRID 2409914노트

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HRID 2409914 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

HCID 70972224HCID 70972224, 화합물수율 48%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-dfe440ed1c464e049ded24fa8671699f
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815909B2

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