p-Fluoronitrobenzene → HCID 54059698, compound

HRID 328392Notes

Reaction equation

HRID 328392 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:9][N:8]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:6]=2[CH:29]=1.[Na][Na].[H-].[Na+].[K].C[C:36]([CH3:39])([O-])[CH3:37].[K+].F[C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:14]([C:20]([O:22][C:37]3[CH:36]=[CH:39][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)=[O:21])[CH2:15][CH2:16][C:17]([O:19][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)=[O:18])[CH2:9][N:8]=[C:7]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:6]=2[CH:29]=1

Participants

8

Reactant 6

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 141233DisodiumHCID 5462222PotassiumHCID 23665647Potassium tert-butoxideHCID 53892927HCID 53892927, compound

Product 1

HCID 54059698HCID 54059698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-chloro-2-[(1,3-biscarboxypropylidene)-hydrazino]-5-phenyl-3H-1,4-benzodiazepine in tetrahydrofuran can be converted to the disodium salt with sodium hydride or to the potassium salt with potassium t-butoxide. To this can be added a solution of p-fluoronitrobenzene and the mixture stirred at 0°-100°. The ester can be isolated by filtering off the sodium (or potassium) fluoride and evaporating the solution or by dissolving the sodium (or potassium fluoride in cold water and extracting the ester with methylene chloride, followed by drying and evaporating the extract to give 7-chloro-2-[[1,3-bis[(p-nitrophenoxy)carbonyl]propylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine.

Sources & evidence

ORD record
ord-85b2e9b612db4d2bb88e432f3e5aa65d
Source dataset
uspto-grants-1977_04
Patent number
US04017492

Reaction notes

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