5-Chloro-2-nitrobenzyl alcohol → 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(5-chloro-2-nitrobenzyloxy)carbonyl]hydrazine

HRID 1637393Notes

Reaction equation

HRID 1637393 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].[CH3:13][S:14]([N:17]([CH2:36][CH2:37][Cl:38])[N:18]([S:32]([CH3:35])(=[O:34])=[O:33])[C:19](OCC1C=CC=CC=1[N+]([O-])=O)=[O:20])(=[O:16])=[O:15]>>[CH3:13][S:14]([N:17]([CH2:36][CH2:37][Cl:38])[N:18]([S:32]([CH3:35])(=[O:33])=[O:34])[C:19]([O:8][CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])=[O:20])(=[O:15])=[O:16]

Participants

3

Reactant 2

HCID 5560665-Chloro-2-nitrobenzyl alcoholHCID 193484121,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(2-nitrobenzyloxy)carbonyl]hydrazine

Product 1

HCID 193484111,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(5-chloro-2-nitrobenzyloxy)carbonyl]hydrazine

Procedure

1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(5-chloro-2-nitrobenzyloxy)carbonyl]hydrazine (compound 13c) was prepared from 5-chloro-2-nitrobenzyl alcohol using a procedure similar to that described for compound 13a. The Mp was approximately 100-102° C., and the yield was approximately 14.6% by weight after recrystallization from ethanol. 1H NMR (acetone-d6): δ 8.2, 8.0 and 7.7 (3H, 2d, s, aromatic H), 5.8 (2H, d, ArCH2), 3.6-4.1 (4H, m, CH2CH2Cl), 3.5 and 3.2 (6H, 2s, 2 CH3SO2).

Workup

  1. customThe Mp was approximately 100-102° C., and the yield was approximately 14.6% by weight after recrystallization from ethanol

Sources & evidence

ORD record
ord-dc16312dc3f54e5ba7ab554ff646b058
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Reaction notes

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