3-Methoxy-4-nitrobenzyl alcohol → 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(3-methoxy-4-nitrobenzyloxy)carbonyl]hydrazine

HRID 1637394Notes

Reaction equation

HRID 1637394 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6][OH:7].[CH3:14][S:15]([N:18]([CH2:37][CH2:38][Cl:39])[N:19]([S:33]([CH3:36])(=[O:35])=[O:34])[C:20](OCC1C=CC=CC=1[N+]([O-])=O)=[O:21])(=[O:17])=[O:16]>>[CH3:14][S:15]([N:18]([CH2:37][CH2:38][Cl:39])[N:19]([S:33]([CH3:36])(=[O:34])=[O:35])[C:20]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:21])(=[O:16])=[O:17]

Participants

3

Reactant 2

HCID 6029613-Methoxy-4-nitrobenzyl alcoholHCID 193484121,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(2-nitrobenzyloxy)carbonyl]hydrazine

Product 1

HCID 193484151,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(3-methoxy-4-nitrobenzyloxy)carbonyl]hydrazine

Procedure

1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(3-methoxy-4-nitrobenzyloxy)carbonyl]hydrazine (compound 13d) was prepared from 3-methoxy-4-nitrobenzyl alcohol using a procedure similar to that described for compound 13a. The Mp was determined to be about 56-57° C., and the yield was about 29.4% by weight after recrystallization from ethanol. 1H NMR (acetone d6): δ 7.8, 7.5 and 7.2 (3H, 2d, s, aromatic H), 5.8 (2H, d, ArCH2), 3.6-4.1 (4H, m, CH2CH2Cl), 4.0 (3H, S, OCH3), 3.6 and 3.3 (6H, 2s, 2 CH3SO2).

Workup

  1. customto be about 56-57° C.
  2. customthe yield was about 29.4% by weight after recrystallization from ethanol

Sources & evidence

ORD record
ord-273e922705b9445086c0943f530c7d7a
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Reaction notes

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