Water → 155272-08-5

HRID 375372Notes

Reaction equation

HRID 375372 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10](/[CH:11]=[CH:12]/[C:13]2[N:21]([CH3:22])[C:20]3[C:19](=[O:23])[N:18]([CH2:24][CH3:25])[C:17](=[O:26])[N:16]([CH2:27][CH3:28])[C:15]=3[N:14]=2)=[CH:9][CH:8]=1.[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C)C=O>[N:31]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10](/[CH:11]=[CH:12]/[C:13]2[N:21]([CH3:22])[C:20]3[C:19](=[O:23])[N:18]([CH2:24][CH3:25])[C:17](=[O:26])[N:16]([CH2:27][CH3:28])[C:15]=3[N:14]=2)=[CH:9][CH:8]=1)=[N+:32]=[N-:33]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 6448951(E)-8-(4-(4-bromobutoxy)styryl)-1,3-diethyl-7-methylxanthine

Product 1

HCID 6448952155272-08-5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 177 (235 mg, 0.49 mmol) obtained in Reference Example 116 was dissolved in 10 ml of dimethylformamide. To the solution was added 161 mg (2.48 mmol) of sodium azide, and the mixture was stirred at 80° C. for 3 hours. Water was added thereto under ice cooling and the deposited crystals were collected by filtration. The collected crude crystals were dissolved in chloroform, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform), followed by recrystallization from hexane/ethyl acetate to give 216 mg (yield quant.) of Compound 178 as pale yellow grains.

Workup

  1. filtrationunder ice cooling and the deposited crystals were collected by filtration
  2. customThe collected crude crystals
  3. dissolutionwere dissolved in chloroform
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform)
  8. customfollowed by recrystallization from hexane/ethyl acetate
  9. customto give

Sources & evidence

ORD record
ord-9f0edb223b7a419896c8ab9140502d48
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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