Ethanol → 6-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil

HRID 396263Notes

Reaction equation

HRID 396263 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:15])[N:5]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:23])[CH:3]=1.O.C(O)C.[N:28]([O-])=[O:29].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:15])[N:5]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:4](=[O:23])[C:3]=1[N:28]=[O:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 222449716-Amino-1,3-bis(cyclohexylmethyl)uracilHCID 23668193Sodium Nitrite

Product 1

HCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Amino-1,3-bis(cyclohexylmethyl)uracil (from step (b), 25.0 g) was dissolved in glacial acetic acid (440 ml), water (440 ml) and ethanol (440 ml) at reflux. To this solution was added sodium nitrite (5.65 g). The resulting mixture was stirred as it cooled slowly to ambient temperature. The lavender precipitate was filtered off, washed with 1:1 water-ethanol and dried to give 6-amino-1,3-bis(cyclohexylmethyl)-5-nitrosouracil as light purple crystals (23.46 g, 86%), m.p. 240-243° C. dec with effervescence; 1H-NMR (DMSO-d6) δ: 13.23 (br s, 1, ═NOH), 9.00 (br s, 1, ═NH), 3.73 (br t, J=6.86, 4, 2 NCH2), 2.0-1.6 and 1.7-1.1 (both m, total 22, 2 cyclohexyl).

Workup

  1. filtrationThe lavender precipitate was filtered off
  2. washwashed with 1:1 water-ethanol
  3. customdried

Sources & evidence

ORD record
ord-fd6c59af1dab4a0b87a458117ae93c97
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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