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

HRID 1419355

반응식

HRID 1419355 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): δ 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-2a2f95818792418da0d21356650fb05b
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886044

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