Hexamethylenetetramine → HCID 22728121, compound

HRID 2086152Notes

Reaction equation

HRID 2086152 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=2[CH3:18])=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:33](O)=[O:34]>>[CH3:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([CH3:14])[C:8]=1[O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:20]([CH:19]=1)[CH:33]=[O:34]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 22728121HCID 22728121, compound

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene (7.0 g, 25.6 mmol) in trifluoroacetic acid (60 mL) at room temperature was added hexamethylenetetramine (5.75 g, 41.0 mmol). The resulting mixture was stirred at 75° C. for 6 hours and then concentrated. To the residue was added water (150 mL), stirred at room temperature for 19 hours, extracted with 10% methanol in methylene chloride (4 times 50 mL) and ethyl acetate (75 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The product (6.56 g) was crystalized from dissolving in a minimum amount of Et2O. 1H NMR (400 MHz, CDCl3) δ10.40 (s, 1H), 8.00 (s, 2H), 7.07-7.04 (s+d, 2H), 6.95 (d, 1H), 3.90 (s, 3H), 2.18 (s, 6H). MS (APCI−) Calc: 301.0, Found: 300.0 (M−1).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added water (150 mL)
  3. stirringstirred at room temperature for 19 hours
  4. extractionextracted with 10% methanol in methylene chloride (4 times 50 mL) and ethyl acetate (75 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product (6.56 g) was crystalized
  9. dissolutionfrom dissolving in a minimum amount of Et2O

Sources & evidence

ORD record
ord-f4c3d4655f78451798a89f71d69eda19
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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