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

HRID 567971Notes

Reaction equation

HRID 567971 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 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.

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-1e7f9d0c0c3a4e86a3d54c680cd9ddbc
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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