Triethylamine → n-(2-Hydroxy-5-nitrophenyl)-n'-(3-methoxy-2-thienyl)urea

HRID 1385343

반응식

HRID 1385343 반응식
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1C(O)=O.[NH2:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].C([N:24]([CH2:27]C)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:30]>C1C=CC=CC=1>[OH:21][C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[NH:11][C:27]([NH:24][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 36133892-Amino-4-Nitrophenol

생성물 1

HCID 15411486n-(2-Hydroxy-5-nitrophenyl)-n'-(3-methoxy-2-thienyl)urea수율 41%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of 3-methoxy-2-thiophene carboxylic acid (200 mg, 1.27 mmol) in benzene, (PhO)2PON3 (0.33 mL), 2-amino-4-nitrophenol (195.7 mg, 1.27 mmol) and triethylamine (1.1 equiv., 0.25 mL) were added. The reaction mixture was stirred at reflux 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 a solid product (160 mg, 41%). mp: 172.6-173.0° C.; 1H NMR (CD3OD/CDCl3): d 8.96 (d, 1H, J=2.5 Hz), 7.74 (dd, 1H, J=5.0 Hz and J=1.25 Hz), 6.82 (d, 1H, J=7.5 Hz), 6.76 (s, 2H), 3.80 (s, 3H); EI-MS m/z 309 (M+H)+; Anal. (C12H11N3O5S) C, H, N.

후처리

  1. temperatureat reflux overnight
  2. customThe reaction mixture was partitioned between 5% citric acid and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a5fbc6afe2554eec8c3b74d4d25ba84e
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262113B1

연결된 노트

불러오는 중…