1,2-Dichloroethane → HCID 11678369, compound

HRID 601467Notes

Reaction equation

HRID 601467 reaction equation
[CH2:1]([C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:39]([NH:41][CH2:42][CH2:43][OH:44])[CH3:40].Cl[CH2:46][CH2:47]Cl>>[CH2:1]([C:8]1[N:16]([CH2:40][CH2:39][N:41]([CH2:46][CH3:47])[CH2:42][CH2:43][OH:44])[C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 80722-(Ethylamino)ethanolHCID 10340Sodium CarbonateHCID 103655718-Benzyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine

Product 1

HCID 11678369HCID 11678369, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 2.1 gm of 8-benzyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine (9), 1.02 gm of sodium carbonate, 3.82 ml of 1,2-dichloroethane and 0.59 ml of 2-(ethylamino)ethanol was heated in a steel pressure vessel under argon at 120 degrees C. for 3-5 hours*. The mixture was then cooled and vented to the atmosphere. The semisolid reaction mixture was triturated several times with 5-10 ml portions of methanol followed by methylene chloride and the combined solutions were evaporated to dryness. The residue was purified by column chromatography on silica gel using a gradient of 1:1 ethyl acetate-hexanes, ethyl acetate and 5% methanol in ethyl acetate. The appropriate fractions were collected and evaporated to dryness to yield a light orange solid of 8-benzyl-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine.

Workup

  1. temperatureThe mixture was then cooled
  2. customThe semisolid reaction mixture
  3. customwas triturated several times with 5-10 ml portions of methanol
  4. customthe combined solutions were evaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel using a gradient of 1:1 ethyl acetate-hexanes, ethyl acetate and 5% methanol in ethyl acetate
  6. customThe appropriate fractions were collected
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-396c7af80eaa403ba03d39e509cd8d7b
Source dataset
uspto-grants-2011_03
Patent number
US07902360B2

Reaction notes

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