Dimethylformamide → HCID 21437213, compound

HRID 2397227Notes

Reaction equation

HRID 2397227 reaction equation
CN(C)C=O.[N+:6]([C:9]1[CH:10]=[C:11]([CH:15]2[C:28]3[C:27](=[O:29])[CH2:26][CH2:25][CH2:24][C:23]=3[NH:22][C:21]3[CH2:20][CH2:19][CH2:18][C:17](=[O:30])[C:16]2=3)[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7].[H-].[Na+].Cl[CH2:34][O:35][CH2:36][CH3:37]>C(O)(=O)C>[CH2:36]([O:35][CH2:34][N:22]1[C:21]2[CH2:20][CH2:19][CH2:18][C:17](=[O:30])[C:16]=2[CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=2)[C:28]2[C:27](=[O:29])[CH2:26][CH2:25][CH2:24][C:23]1=2)[CH3:37]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 667553HCID 667553, compound

Product 1

HCID 21437213HCID 21437213, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

In 10 ml. of dimethylformamide was suspended 0.5 g. of 9-(3-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridine and after adding to the suspension 0.2 g. of a 50% oil dispersion of sodium hydride, the mixture was stirred for 1.5 hours at room temperature. After cooling the mixture to -10° C., 0.5 ml. of chloromethoxyethane was added thereto, the temperature of the mixture was elevated to room temperature over a period of about 20 minutes, stirred for 2 hours and the mixture was cooled again to -10° C. Then, after adding to the reaction product 0.5 ml. of glacial acetic acid and 20 ml. of water, the product was extracted three times each time with 5 ml. of ether. The extracts were combined, washed with 5 ml. of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then ether was distilled away. The residue became crystallized by the addition of 5 ml. of ethanol. The crystals were filtered, dissolved in 2 ml. of chloroform and recrystallized by the addition of ethanol and 0.4 g. of pale brown prismatic crystals of 10-ethoxymethyl-9-(3-nitrophenyl)-1,8-dioxo- 1,2,3,4,5,6,7,8,9,10-decahydroacridine melting at 222° C. were obtained.

Workup

  1. temperaturethe mixture was cooled again to -10° C
  2. extractionof water, the product was extracted three times each time with 5 ml
  3. washwashed with 5 ml
  4. dry with materialof saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate
  5. distillationether was distilled away
  6. customThe residue became crystallized by the addition of 5 ml
  7. filtrationThe crystals were filtered
  8. dissolutiondissolved in 2 ml
  9. customof chloroform and recrystallized by the addition of ethanol and 0.4 g

Sources & evidence

ORD record
ord-2f481f902a304ec4906152aa332f71b3
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

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