Water → 8-Amino-1,3-di(cyclopropylmethyl)-7-(4-nitrobenzenesulphonyl)xanthine

HRID 1654696Notes

Reaction equation

HRID 1654696 reaction equation
[NH2:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH:13]3[CH2:15][CH2:14]3)[C:6](=[O:16])[N:5]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[C:4]=2[N:3]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22].C(N(CC)CC)C.O>O1CCCC1>[NH2:1][C:2]1[N:10]([S:30]([C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=2)(=[O:31])=[O:32])[C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[C:6](=[O:16])[N:5]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 71356Cipamfylline

Product 1

HCID 100044228-Amino-1,3-di(cyclopropylmethyl)-7-(4-nitrobenzenesulphonyl)xanthine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Amino-1,3-di(cyclopropylmethyl)xanthine (2.7 g, 10 mmol), 4-nitrobenzenesulphonyl chloride (5.5 g, 25 mmol) and triethylamine (3 ml, 20 mmol) were stirred together in tetrahydrofuran (THF) (40 ml) at ambient temperature for 24 hr. After adding to water (100 ml) the mixture was extracted into ethyl acetate (150 ml) and the organic solution dried (MgSO4) and evaporated. Chromatography of the residue on silica, (hexane/acetone gradient) gave 8-amino- 1,3-di(cyclopropylmethyl)-7-(4-nitrobenzenesulphonyl)xanthine followed by 1,3-di(cyclopropylmethyl)-8di(cyclopropylmethyl)-8-di(4-nitrobenzenesulphonyl)aminoxanthine.

Workup

  1. extractionwas extracted into ethyl acetate (150 ml)
  2. dry with materialthe organic solution dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-e9862a9554f74488aee4ecc181f812af
Source dataset
uspto-grants-1995_04
Patent number
US05409934

Reaction notes

Loading…