Chlorosulfonyl isocyanate → Methyl 3-carbamoyl-4,7-dimethylindole-2-carboxylate

HRID 361618Notes

Reaction equation

HRID 361618 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.ClS([N:20]=[C:21]=[O:22])(=O)=O>C(#N)C>[C:21]([C:4]1[C:3]2[C:7](=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[CH3:1])[NH:6][C:5]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:22])[NH2:20]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylate

Product 1

HCID 54419776Methyl 3-carbamoyl-4,7-dimethylindole-2-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.0 g (9.9 mmol) of methyl 4,7-dimethylindole-2-carboxylate in 200 ml of anhydrous acetonitrile was cooled to 0° C. A solution of 3 ml (9.9 mmol) of chlorosulfonylisocyanate in 50 ml of anhydrous acetonitrile was added dropwise over a period of 15 minutes and the reaction mixture was stirred at room temperature for 30 minutes. After distilling off acetonitrile under reduced pressure, the residue was dissolved in 15 ml of acetonitrile-water (4:1). The pH of the solution was adjusted to 8 by gradually adding 10% potassium hydroxide aqueous solution dropwise. The white crystals precipitated were separated by filtration and air-dried and then dried under reduced pressure to provide 1.0 g of white crystals.

Workup

  1. distillationAfter distilling off acetonitrile under reduced pressure
  2. dissolutionthe residue was dissolved in 15 ml of acetonitrile-water (4:1)
  3. additionby gradually adding 10% potassium hydroxide aqueous solution dropwise
  4. customThe white crystals precipitated
  5. customwere separated by filtration
  6. customair-dried
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f755a1d1fd9d4a2ba57eacb51c03eeaf
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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