Sodium Nitrate → (4-Chlorosulfonyl-2-nitro-phenyl)-carbamic acid ethyl ester

HRID 2182432

Reaction equation

HRID 2182432 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[N+:17]([O-])([O-:19])=[O:18].[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:16])[NH:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([Cl:15])(=[O:13])=[O:14])=[CH:10][C:11]=1[N+:17]([O-:19])=[O:18])[CH3:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 256294(4-Chlorosulfonyl-phenyl)-carbamic acid ethyl ester

Product 1

HCID 12963055(4-Chlorosulfonyl-2-nitro-phenyl)-carbamic acid ethyl esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a stirred suspension of (4-chlorosulfonyl-phenyl)-carbamic acid ethyl ester (5 g, Reference Example 64) in concentrated sulfuric acid (25 ml) at 0° C., was added dropwise a suspension of sodium nitrate (1.61 g) in concentrated sulfuric acid and the reaction stirred for 3 hours. The reaction mixture was then poured onto ice, the resultant precipitate collected by filtration and dried in vacuo to give (4-chlorosulfonyl-2-nitro-phenyl)-carbamic acid ethyl ester (4.80 g) as a yellow solid. LC-MS (METHOD B): RT=3.32 minutes, 307.08 (M−H)−.

Workup

  1. additionwas added dropwise
  2. additionThe reaction mixture was then poured onto ice
  3. filtrationthe resultant precipitate collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3c414788c54246529571e2fddd1e4d65
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Linked notes

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