Water → HCID 19834632, compound

HRID 1087692Notes

Reaction equation

HRID 1087692 reaction equation
C([O-])(=O)C.[NH4+].Cl.[CH2:7]([O:9][C:10]1[C:15]([NH2:16])=[C:14]([O:17][CH2:18][CH3:19])[C:13]([NH2:20])=[CH:12][C:11]=1[Cl:21])[CH3:8].O.C(N(CC)CC)C>[Pd].C(O)C.C(O)=O>[ClH:21].[NH2:16][C:15]1[C:14]([O:17][CH2:18][CH3:19])=[C:13]([NH2:20])[CH:12]=[CH:11][C:10]=1[O:9][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 19834631HCID 19834631, compound

Product 1

HCID 19834632HCID 19834632, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The mixture consisting of 7.7 g of ammonium acetate, 3.8 g of 10% palladium on charcoal, 0.025 mole (7.6 g) of 2,4-diethoxy-3,5-diaminochlorobenzene hydrochloride in 42 ml of ethanol containing 5 ml of water was heated to 70° C. with stirring. 7.5 g of triethylamine were added and then, 3.1 g of formic acid were added dropwise. After 20 additional minutes of heating at 80° C., the reaction mixture was filtered while hot. The filtrate was evaporated to dryness. Upon addition of ethyl acetate, the inorganic salts were precipitated and removed by filtration. 10 ml of a 7N alcoholic solution of hydrochloric acid were added to the filtrate which was dried over sodium sulphate. The expected product precipitated; it was recrystallized from a 6N hydrochloric acid solution.

Workup

  1. temperatureAfter 20 additional minutes of heating at 80° C.
  2. filtrationthe reaction mixture was filtered while hot
  3. customThe filtrate was evaporated to dryness
  4. additionUpon addition of ethyl acetate
  5. customthe inorganic salts were precipitated
  6. customremoved by filtration
  7. addition10 ml of a 7N alcoholic solution of hydrochloric acid were added to the filtrate which
  8. dry with materialwas dried over sodium sulphate
  9. customThe expected product precipitated
  10. customit was recrystallized from a 6N hydrochloric acid solution

Sources & evidence

ORD record
ord-849a64f642cc442484c35057684c4896
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

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