Hydrochloric Acid → N-(2,4-dichloro-5-hydrazinylbenzyl)-2,2-dimethylpropanamide

HRID 59381Notes

Reaction equation

HRID 59381 reaction equation
N[C:2]1[CH:15]=[C:14]([Cl:16])[C:13]([NH2:17])=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=O)[C:7]([CH3:10])([CH3:9])[CH3:8].[N:18]([O-])=O.[Na+].[OH2:22].O.Cl[Sn]Cl.[ClH:27]>>[Cl:27][C:2]1[CH:15]=[C:14]([Cl:16])[C:13]([NH:17][NH2:18])=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:22])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 90019665N-(2,5-diamino-4-chlorobenzyl)pivalamide

Product 1

HCID 90019848N-(2,4-dichloro-5-hydrazinylbenzyl)-2,2-dimethylpropanamide

Procedure

The title compound was prepared according to the procedure described in step-1 of Intermediate-61 by using N-(2,5-diamino-4-chlorobenzyl)pivalamide (1.5 g, 5.8 mmol), NaNO2 (0.481 g, 6.9 mmol), SnCl2.2H2O (3.20 g, 14.5 mmol), conc. HCl (50 mL) to afford 1.0 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.11 (s, 9H), 4.44 (m, 2H), 6.53 (m, 1H), 7.18 (m, 1H), 7.99 (m, 1H), 10.23 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e6435beadf9b49f2859f2a6803d925c8
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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