HCID 54530667, compound → 202584-20-1

HRID 442750Notes

Reaction equation

HRID 442750 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([N:14]=[N+]=[N-])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[NH:14][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)=[O:17]

Participants

3

Reactant 1

HCID 54530667HCID 54530667, compound

Product 1

HCID 4715405202584-20-1Yield 61%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of methyl-2-azido-3-(4-methylthiophenyl)-propenoate (20.6 g, 83 mmol) in xylene (200 ml) was added dropwise to boiling xylene (250 ml) over a period of 2 hours. The reaction mixture was allowed to heat at reflux temperature for an additional 2 hours, then cooled slowly and placed in a freezer overnight. The solids were filtered, washed with a small amount of CH2Cl2 /hexane (1:3) and dried to give 11.2 g (61.0%) of methyl-6-methylsulfanyl-1H-indole-2-carboxylate.

Workup

  1. customof 2 hours
  2. temperatureto heat
  3. temperatureat reflux temperature for an additional 2 hours
  4. temperaturecooled slowly
  5. filtrationThe solids were filtered
  6. washwashed with a small amount of CH2Cl2 /hexane (1:3)
  7. customdried

Sources & evidence

ORD record
ord-6258c3a9dedf41b79bbeea86ecd0730a
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

Loading…