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

HRID 1956627Notes

Reaction equation

HRID 1956627 reaction equation
[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]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 14834753-Methoxythiophene-2-carboxylic acidHCID 36133892-Amino-4-Nitrophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-methoxy-2-thiophene carboxylic acid (200 mg, 1.27 mnmol) 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.

Workup

  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

Sources & evidence

ORD record
ord-cb677a95aea84071b9725d68dc27f74b
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

Loading…