p-Tolyl chloroformate → 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-tolyloxy)carbonyl]hydrazine

HRID 1637386

Reaction equation

HRID 1637386 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:3].[CH3:12][S:13]([N:16]([CH2:31][CH2:32][Cl:33])[N:17]([S:27]([CH3:30])(=[O:29])=[O:28])C(OC1C=CC=CC=1)=O)(=[O:15])=[O:14]>>[CH3:12][S:13]([N:16]([CH2:31][CH2:32][Cl:33])[N:17]([S:27]([CH3:30])(=[O:29])=[O:28])[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:3])(=[O:14])=[O:15]

Participants

3

Reactant 2

HCID 70304p-Tolyl chloroformateHCID 97995471,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-(phenoxycarbonyl)hydrazine

Product 1

HCID 98430801,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-tolyloxy)carbonyl]hydrazine

Procedure

1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(4-tolyloxy)carbonyl]hydrazine (compound 10e) was prepared by reacting compound 2 with 4-tolyl chloroformate using a procedure similar to that employed for compound 10d. The product was recrystallized from ethanol, and the yield was about 31.2% by weight. The Mp was approximately 85-86° C. 1H NMR (CDCl3): δ 7.3 and 7.1 (4H, 2d, aromatic H), 3.7-4.2 (4H, m, CH2CH2Cl), 3.5 and 3.2 (6H, 2s, 2 CH3SO2), 2.4 (3H, s, ArCH3).

Workup

  1. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c4c54a8ddc474c74a71c80c6bb9c9e67
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Linked notes

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