1,2-Dichloro-4-nitrobenzene → 1,3-dimethyl-6-{4-[3-(2-chloro-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

HRID 1085278Notes

Reaction equation

HRID 1085278 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17](S(CC)(=O)=O)[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:32])[N:4]([CH3:33])[C:3]1=[O:34].[Cl:35]C1C=C([N+]([O-])=O)C=CC=1Cl.C(N(CC)CC)C>CN(C)C=O>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=3[Cl:35])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:32])[N:4]([CH3:33])[C:3]1=[O:34]

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 8471TriethylamineHCID 200610721,3-dimethyl-6-{4-[3-(N-ethanesulfonyl-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 200612471,3-dimethyl-6-{4-[3-(2-chloro-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedioneYield 155.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 0.4 g of Compound 158 obtained in Example 99-(1), 0.4 g of 3,4-dichloro-nitrobenzene, 0.43 ml of triethylamine and 6 ml of dimethylformamide was treated in a manner similar to Example 99-(2), thereby obtaining 0.55 g of 1,3-dimethyl-6-{4-[3-(2-chloro-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. additionwas treated in a manner similar to Example 99-(2)

Sources & evidence

ORD record
ord-45f9cada9c2e4d18ab79196b2e09ebfc
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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