Water → HCID 50994291, compound

HRID 1518041Notes

Reaction equation

HRID 1518041 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](F)=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH3:15][CH2:16][N:17](C(C)C)[CH:18](C)[CH3:19].C(NCC)C.O>C1COCC1>[NH2:6][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([N:17]([CH2:18][CH3:19])[CH2:16][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 739445-Fluoro-2,4-dinitroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 50994291HCID 50994291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,4-dinitro-5-fluoroaniline (1.6 g, 8.0 mmol) in 20 mL of THF, a mixture of DIPEA (1.1 g, 8.8 mmol) and diethylamine (644 mg, 8.8 mmol) in 5 mL of THF was added slowly. The reaction mixture was stirred at room temperature for 1 h. Water (100 mL) was added to give the desired product as a yellow precipitate. The product was collected by filtration and washed with water (200 mL). The filtrate was concentrated to dryness in vacuo to give the desired product (1.8 g, 90% yield) as a bright yellow solid: 1H-NMR (300 MHz, CDCl3) δ 1.96 (t, 6H, J=7.2 Hz), 3.24 (q, 4H, J=7.2 Hz), 6.08 (s, 1H), 8.75 (s, 1H); 13C NMR (75 MHz, CDCl3) δ12.1, 45.7, 102.7, 123.3, 128.2, 131.6, 147.8, 149.4; ESI MS m/z 255.1 [M+H]+.

Workup

  1. additionwas added slowly

Sources & evidence

ORD record
ord-03981beee29d407a88e1aa7a40b7c28b
Source dataset
uspto-grants-2012_07
Patent number
US08232410B2

Reaction notes

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