1,1'-Carbonyldiimidazole → HCID 178503270, compound

HRID 1417509Notes

Reaction equation

HRID 1417509 reaction equation
C([N:8]1[CH:12]=CN=C1)(N1C=CN=C1)=O.[CH2:13]([N:20]1[C:32]2[C:31]([S:33][CH3:34])=[C:30]([CH2:35][C:36]([OH:38])=O)[CH:29]=[C:28]([CH3:39])[C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[S:41](N)(=[O:43])=[O:42].N12CCCN=C1CCCCC2>O1CCCC1.O>[CH2:13]([N:20]1[C:32]2[C:31]([S:33][CH3:34])=[C:30]([CH2:35][C:36]([CH2:12][NH:8][SH:41](=[O:43])=[O:42])=[O:38])[CH:29]=[C:28]([CH3:39])[C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54170692HCID 54170692, compound

Product 1

HCID 178503270HCID 178503270, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

74.6 mg (0.26 mmol) of carbonyldiimidazole was added to 1 ml of a solution of 50 mg (0.13 mmol) of (9-benzyl-4-methyl-1-methylthiocarbazol-2-yl)acetic acid, as obtained in Example 14, in tetrahydrofuran, and the reaction mixture was stirred for 1 hour at room temperature. After this time, 43.8 mg (0.26 mmol) of methanesulfonamide and 70.0 mg (0.26 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to the mixture which was first stirred overnight at room temperature and then refluxed for 2 hours. After this time, an excess of water was added to the mixture, and the resulting aqueous layer was extracted with ethyl acetate. The extracted organic layer was first washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and the solvent was then removed by evaporation under reduced pressure. The residue was subjected to column chromotography (eluent: a 50% v/v solution of ethyl acetate in hexane) to yield 48 mg (80%) of the title compound.

Workup

  1. waitwas first stirred overnight at room temperature
  2. temperaturerefluxed for 2 hours
  3. extractionthe resulting aqueous layer was extracted with ethyl acetate
  4. washThe extracted organic layer was first washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  6. customthe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-94cd93fcedff49178a30da8cd64c7bc2
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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