Water → HCID 136336801, compound

HRID 576497Notes

Reaction equation

HRID 576497 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:22]3[CH:21]=[CH:20][C:19]4[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=4[C:17]=3[N:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]2[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=23)=[CH:5][CH:4]=1.Cl.[NH+]1C=CC=CC=1.O>C(Cl)(Cl)Cl>[CH:27]1[C:14]2[C:15]3[N:16]=[C:17]4[C:22]([CH:21]=[CH:20][C:19]5[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=54)=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=4)[C:10]=3[CH:11]=[CH:12][C:13]=2[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21584435Pyridinium hydrochlorideHCID 86691487HCID 86691487, compound

Product 1

HCID 136336801HCID 136336801, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
210 °C

Procedure

In a pressure vessel a mixture of 18 (1.00 g, 2.6 mmol, 1 eq) and pyridiniumhydrochloride (1.75 g, 15.1 mmol, 5.8 eq) was heated to 210° C. under an inert atmosphere and vigorously stirred at this temperature over a three days period. The mixture was allowed to cool down to room temperature. The solidified melt was dissolved in chloroform (50 mL) and water (50 mL) and treated in an ultrasonic bath for 5 minutes. The layers were separated and the aqueous layer was extracted with chloroform (3×50 mL). Afterwards, the combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution (5×50 mL) followed by water (3×50 mL) and dried over magnesium sulphate. Evaporation of the solvent at 40° C. led to an old rose coloured solid. The product was directly used in the next step without any further purification.

Workup

  1. temperatureto cool down to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with chloroform (3×50 mL)
  4. washAfterwards, the combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution (5×50 mL)
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation of the solvent at 40° C.
  7. customThe product was directly used in the next step without any further purification

Sources & evidence

ORD record
ord-b7424edb53394f778bfee2f350d9045a
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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