2-Aminobenzophenone → HCID 57632408, compound

HRID 2108683Notes

Reaction equation

HRID 2108683 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C(N(CC)C(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:20])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 760802-AminobenzophenoneHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 57632408HCID 57632408, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) solution of 2,4-dichloro-5-nitropyrimidine (0.53 g, 2.75 mmol) in THF (3 mL) was added a solution of (2-aminophenyl)(phenyl)methanone (0.30 g, 1.55 mmol) and N,N-diisopropylethylamine (0.5 mL, 3.0 mmol) in THF (2.0 mL). The reaction was stirred for 2.0 hours. The reaction was then poured onto ice and allowed to warm to room temperature then was filtered, washing the solid with water. The isolated solid was dried under vacuum to give {2-[(2-chloro-5-nitropyrimidin-4-yl)amino]phenyl}(phenyl)methanone (496 mg, 90%) as a yellow solid. 1H NMR (DMSO-d6/D2O): δ 9.06 (s, 1H), 7.96 (d, 1H), 7.76-7.44 (m, 8 H). MS m/z 354 (M+1).

Workup

  1. additionThe reaction was then poured onto ice
  2. filtrationthen was filtered
  3. washwashing the solid with water
  4. customThe isolated solid was dried under vacuum

Sources & evidence

ORD record
ord-9614e4195e67429cb4ba51511c27d41a
Source dataset
uspto-grants-2009_04
Patent number
US07514446B2

Reaction notes

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