6-Amino-1-(4-chloro-benzyl)-1H-pyrimidine-2,4-dione → 6-Amino-1-[(4-chlorophenyl)methyl]-5-nitroso-2,4(1H,3H)-pyrimidinedione

HRID 2288660Notes

Reaction equation

HRID 2288660 reaction equation
[N:1]([O-:3])=O.[Na+].[NH2:5][C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10](=[O:20])[NH:9][C:8](=[O:21])[CH:7]=1>C(O)(=O)C>[NH2:5][C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10](=[O:20])[NH:9][C:8](=[O:21])[C:7]=1[N:1]=[O:3]

Participants

4

Reactant 2

HCID 15266206-Amino-1-(4-chloro-benzyl)-1H-pyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 184328276-Amino-1-[(4-chlorophenyl)methyl]-5-nitroso-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

157.6 ml of 4N sodium nitrite was added over 45 minutes to a suspension of 165 g of 6-amino-1-(4-chlorobenzyl)-uracil in 825 ml of acetic acid at 65-70° C. After a further 15 minutes at 70° C. the reaction mixture was cooled to room temperature, the pink solid collected and washed with 80% acetic acid and water to give the title compound (150.9 g) mp >320° C.

Workup

  1. customthe pink solid collected
  2. washwashed with 80% acetic acid and water

Sources & evidence

ORD record
ord-b20558b7e5bd47aabf9fcbe355bc55a1
Source dataset
uspto-grants-2000_07
Patent number
US06090816

Reaction notes

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