N,N-Diethylaniline → HCID 59458015, compound

HRID 547569Notes

Reaction equation

HRID 547569 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)=[N:6][CH:7]=1.C(N(CC)C1C=CC=CC=1)C.[N+:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)([O-:30])=[O:29]>O1CCOCC1>[NH2:16][C:11]1[N:10]=[C:9]([NH:8][C:5]2[N:6]=[CH:7][C:2]([NH:1][C:35](=[O:36])[C:34]3[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:39][CH:38]=3)=[CH:3][CH:4]=2)[CH:14]=[C:13]([CH3:15])[N:12]=1

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 85024-Nitrobenzoyl chloride2×HCID 59457944HCID 59457944, compound2×

Product 1

HCID 59458015HCID 59458015, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 10 (500 mg, 2.31 mmol) and N,N-diethylaniline (1 ml, 1.5 eq) in 1,4-dioxane (20 ml) at 0° C. was added dropwise a solution of p-nitrobenzoylchloride (429 mg, 12.31 mmol). The reaction mixture was stirred at 20° C. for 2 h. TLC and mass spectrum showed still presence of 10. Therefore more p-nitrobenzoylchloride (43 mg, 0.1 eq ) was added and stirred for 20 h. The resulting precipitate was filtered and washed with more 1,4-dioxane. The collected solid was stirred in aqueous NH3, filtered washed with water and dried to give essentially pure 11 (821 mg, 97%); mp (MeOH)>300° C.; 1H NMR [(CD3)2SO] δ 10.58 (s, 1 H, NH), 9.56 (s, 1 H, NH), 8.65 (d, J=2.5 Hz, 1 H, H-2′), 8.38 (d, J=8.9 Hz, 2 H, H-3,5), 8.20 (d, J=9.2 Hz, 2 H, H-2,6), 8.17 (d, J=9.1 Hz, 1 H, H-5′), 8.02 (dd, J=9.0, 2.6 Hz, 1H, H-4′), 6.45 (s, 1 H, H-5″), 6.15 (s, 2 H, NH2), 2.12 (s, 3 H, CH3); HRMS (FAB+) (M+1) m/z calc. for C17H16N7O3 (M+1) m/z, 366.1315, found 366.1314; Anal. calc. for C17H15N7O3: C, 55.9; H, 4.1; N, 26.8, found C, 55.6; H, 4.2; N, 26.8%.

Workup

  1. stirringstirred for 20 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with more 1,4-dioxane
  4. stirringThe collected solid was stirred in aqueous NH3
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bbc5c6da002947578112ae65aa142364
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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