Pyridine → Methyl 5-tert-butyl-3-(3-p-tolylureido)furan-2-carboxylate

HRID 1698902노트

반응식

HRID 1698902 반응식
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]=1[C:15]([O:17][CH3:18])=[O:16].N1C=CC=CC=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:15]([C:7]1[O:8][C:9]([C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:10][C:6]=1[NH:5][C:1]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)=[O:2])([O:17][CH3:18])=[O:16]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 6371PhosgeneHCID 7813p-ToluidineHCID 18322376Methyl 3-amino-5-(tert-butyl)furan-2-carboxylate

생성물 1

HCID 9905562Methyl 5-tert-butyl-3-(3-p-tolylureido)furan-2-carboxylate수율 96.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Phosgene (1.93M in toluene, 1.3 mL, 2.5 mmol, 10 equiv) was added rapidly to a solution of methyl 3-amino-5-tert-butylfuran-2-carboxylate (0.050 g, 0.25 mmol) and anh. pyridine (1.0 mL) in anh. toluene (5 mL) at room temp. After 30 min, the orange suspension was concentrated under reduced pressure, then successively charged with dry toluene (1 mL) and concentrated (2×). Finally, anh. toluene (3 mL) was added followed by p-toluidine (0.100 g, 0.93 mmol, 3.7 equiv). The orange mixture was stirred overnight, diluted with EtOAc, washed with a 1M HCl solution and a concentrated NaCl solution, then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography to give N-(2-carbomethoxy-5-tert-butyl-3-furyl)-N′-(4-methylphenyl)urea (0.080 g, 96%) as a pale yellow oil: 1H NMR (CDCl3) δ1.28 (s, 9H), 2.30 (s, 3H), 3.77 (s, 3H), 7.02 (s, 1H), 7.11 (d, J=8.1 Hz, 2H), 7.27 (d, J=8.1 Hz, 2H), 7.87 (br s, 1H), 8.68 (br s, 1H); 13C NMR (CDCl3) δ20.6, 28.3 (3C), 33.0, 51.0, 100.1, 121.4 (2C), 126.0, 129.5 (2C), 134.0, 134.8, 137.7, 152.5, 160.5, 168.2; FTIR (neat) 3400-3200 (br, m), 2966 (s), 1676 (s), 1622 (s), 1536 (s), 1306 (s), 1097 (m) cm−1.

후처리

  1. concentrationthe orange suspension was concentrated under reduced pressure
  2. additionsuccessively charged with dry toluene (1 mL)
  3. concentrationconcentrated (2×)
  4. additionFinally, anh. toluene (3 mL) was added
  5. washwashed with a 1M HCl solution
  6. dry with materiala concentrated NaCl solution, then dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-6bf21a4539f34282b9ef3d1e01ab68e0
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344476B1

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