Ethanol → 4,5-Dimethyl-3-nitro-2-N-pentan-3-ylbenzene-1,2-diamine

HRID 2083629Notes

Reaction equation

HRID 2083629 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([CH3:16])=[C:9]([CH3:17])[C:8]=1[N+:18]([O-:20])=[O:19])[CH2:4][CH3:5])[CH3:2].C(O)C.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].C(=O)(O)[O-].[Na+]>O>[CH2:1]([CH:3]([NH:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([CH3:17])[C:10]([CH3:16])=[CH:11][C:12]=1[NH2:13])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 38479PendimethalinHCID 73972Sodium sulfide nonahydrateHCID 516892Sodium Bicarbonate

Product 1

HCID 151866274,5-Dimethyl-3-nitro-2-N-pentan-3-ylbenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

N-(1-Ethylpropyl)-2,6-dinitro-3,4-xylidine (100 g.) is dissolved in 2500 ml. of ethanol and a solution of sodium sulfide nonahydrate (240 g.) and sodium bicarbonate (84 g.) in 500 ml. of water is added at 25°-42° C. The mixture is heated to 65° C. and held at 60°-65° C. for 3 hours. The mixture is then poured into water and extracted 3 times with 1 liter portion of ether. The ether extracts are combined and dried over magnesium sulfate. Removal of the drying agent and solvent leaves a dark solid which is recrystallized 3 times from hexane and then 3 times from hexane-ethanol. The product (35.0 g.), an orange solid, has m.p. 80°-82° C. Analysis Calcd. for C13H21N3O2 : C, 62.12; H, 8.41; N, 16.71. Found: C, 62.41; H, 8.33; N, 16.47.

Workup

  1. extractionextracted 3 times with 1 liter portion of ether
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the drying agent and solvent
  4. customleaves a dark solid which
  5. customis recrystallized 3 times from hexane

Sources & evidence

ORD record
ord-449573a47e1347739fb60119aacf83f3
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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