Sodium Carbonate → (2-Bromo-4-methyl-5-(trifluoromethyl) benzyl) (3,5-bis(trifluoromethyl) benzyl) cyanamide

HRID 2075041노트

반응식

HRID 2075041 반응식
[Br:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:36]#[C:37]Br>CO>[Br:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:22]([C:26]([F:27])([F:28])[F:29])=[CH:21][C:3]=1[CH2:4][N:5]([CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=[C:9]([C:17]([F:18])([F:19])[F:20])[CH:8]=1)[C:37]#[N:36]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 58968728N-(2-Bromo-4-methyl-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

생성물 1

HCID 86615049(2-Bromo-4-methyl-5-(trifluoromethyl) benzyl) (3,5-bis(trifluoromethyl) benzyl) cyanamide수율 97.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-(2-Bromo-4-methyl-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine (89 mg, 0.180 mmol) was dissolved in methanol (10 mL). To this solution was added sodium carbonate (53.9 mg, 0.396 mmol) followed by cyanogen bromide (5.0M solution in acetonitrile, 21.9 mg, 0.041 mL, 0.207 mmol). The solution stirred at room temperature for 20 hours then concentrated under reduced pressure to dryness. The residue was partitioned between water (10 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL), the organics were combined and dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (97.5%). 1H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H) 7.72 (s, 2H) 7.54 (s, 1H) 7.51 (s, 1H) 4.34(s, 4H) 2.45(s, 3H). LC-MS calc. 519, found 520 (M+H)

후처리

  1. concentrationthen concentrated under reduced pressure to dryness
  2. customThe residue was partitioned between water (10 mL) and ethyl acetate (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2634551154a747d4818bfebd476540ce
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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