4-Nitrobenzyl chloroformate → 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-nitrobenzyloxy)carbonyl]hydrazine

HRID 1637389

Reaction equation

HRID 1637389 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].[CH3:15][S:16]([N:19]([CH2:34][CH2:35][Cl:36])[N:20]([S:30]([CH3:33])(=[O:32])=[O:31])C(OC1C=CC=CC=1)=O)(=[O:18])=[O:17]>>[CH3:15][S:16]([N:19]([CH2:34][CH2:35][Cl:36])[N:20]([S:30]([CH3:33])(=[O:32])=[O:31])[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3])(=[O:17])=[O:18]

Participants

3

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 97995471,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-(phenoxycarbonyl)hydrazine

Product 1

HCID 99323921,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-nitrobenzyloxy)carbonyl]hydrazine

Procedure

1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-nitrobenzyloxy)carbonyl]hydrazine (compound 10h) was prepared by reacting compound 2 with 4-nitrobenzyl chloroformate using a procedure similar to that employed for compound 10d. The product was recrystallized from ethanol, and the yield was approximately 22.9% by weight. The Mp was approximately 132-133° C. 1H NMR (acetone-d6): δ 8.3 and 7.8 (4H, 2d, aromatic H), 5.6 (2H, s, ArCH2), 3.6-4.2 (4H, m, CH2CH2Cl), 3.6 and 3.3 (6H, 2s, 2 CH3SO2).

Workup

  1. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-f3bb101c90294d8589705339f41f8b80
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Linked notes

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