1,2-Dichloroethane → HCID 11678369, compound

HRID 1296588Notes

Reaction equation

HRID 1296588 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. waitfor 3–5 hours*
  2. temperatureThe mixture was then cooled
  3. customThe semisolid reaction mixture
  4. customwas triturated several times with 5–10 ml portions of methanol
  5. customthe combined solutions were evaporated to dryness
  6. 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
  7. customThe appropriate fractions were collected
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-63425db14a1b4236a40c973a03688f23
Source dataset
uspto-grants-2007_07
Patent number
US07247639B2

Reaction notes

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