Triethylamine → n-(2-Hydroxy-4-nitrophenyl)-n'-(3-methoxy-2-thienyl)urea

HRID 1419356노트

반응식

HRID 1419356 반응식
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1C(O)=O.C([N:13]([CH2:16]C)CC)C.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[OH:28].P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:30]>C1(C)C=CC=CC=1>[OH:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[NH:18][C:16]([NH:13][C:4]1[S:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1])=[O:30]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 14834753-Methoxythiophene-2-carboxylic acidHCID 49847212-Amino-5-Nitrophenol

생성물 1

HCID 21184722n-(2-Hydroxy-4-nitrophenyl)-n'-(3-methoxy-2-thienyl)urea수율 48%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
70 °C

실험 절차

To a solution of 3-methoxy-2-thiophene carboxylic acid (example 11a, 200 mg, 1.27 mmol) in toluene, (PhO)2PON3 (0.33 mL) and triethylamine (1.1 equiv., 0.25 mL) were added. The reaction mixture was stirred at 70° C. for 2 hours and cooled down to room temperature then 2-amino-5-nitrophenol was added. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatography of the resulting solid on silica gel (hexane:ethyl acetate;1:1) gave the product (190 mg, 48%). 1H NMR (CD3OD/CDCl3): δ 8.38 (d, 1H, J=5.0 Hz), 7.85 (dd, 1H, J=5.0 Hz and J=1.25 Hz), 7.76 (d, 1H, J=2.5 Hz), 6.9 (s, 2H), 3.95 (s, 3H); EI-MS m/z 309 (M+H)+ ; Anal. (C12H11N3O5S) C, H, N.

후처리

  1. temperaturecooled down to room temperature
  2. stirringThe reaction mixture was stirred at 70° C. overnight
  3. customThe reaction mixture was partitioned between 5% citric acid and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2e53d44589da4574bac2e51051b8a4ad
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886044

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