Sodium Sulfate → 1-carbamoylmethyl-5-nitro-1H-indole-3-sulfonyl chloride

HRID 23406Notes

Reaction equation

HRID 23406 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].S([O-])([O-])(=O)=[O:7].[Na+].[Na+].[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][C:26]#[N:27])[CH:20]=[CH:19]2)([O-:15])=[O:14]>C(Cl)Cl>[C:26]([CH2:25][N:21]1[C:22]2[C:18](=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=2)[C:19]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:20]1)(=[O:7])[NH2:27]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 24638Chlorosulfonic acidHCID 22574036(5-Nitro-indol-1-yl)-acetonitrile

Product 1

HCID 225739891-carbamoylmethyl-5-nitro-1H-indole-3-sulfonyl chlorideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonic acid (3.05 ml, 45.9 mmole) from the above Step was added to a suspension of anhydrous sodium sulfate (0.71 g) in methylene chloride (30 ml). After stirring for 25 minutes at room temperature, (5-nitro-indol-1-yl)-acetonitrile (1.00 g) dissolved in methylene chloride was added via syringe. After stirring for 2 h, the reaction mixture was worked up by the cautious addition of ice. When the ice had melted, the mixture was filtered to afford an off-white powder which was washed well with water to afford 0.806 g of 1-carbamoylmethyl-5-nitro-1H-indole-3-sulfonyl chloride (51% yield).

Workup

  1. additionwas added via syringe
  2. stirringAfter stirring for 2 h
  3. additionthe reaction mixture was worked up by the cautious addition of ice
  4. filtrationthe mixture was filtered
  5. customto afford an off-white powder which
  6. washwas washed well with water

Sources & evidence

ORD record
ord-1c98694ec1084081892f94b60d78dd43
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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