1,1'-Carbonyldiimidazole → HCID 19886429, compound

HRID 654763Notes

Reaction equation

HRID 654763 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[C:7]([C:9]([OH:11])=O)=[CH:8][C:5]=2[CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:28][C:29]1[CH:43]=[CH:42][C:32]2[C:33]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[N:34][O:35][C:31]=2[CH:30]=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[C:7]([C:9]([N:39]3[CH2:38][CH2:37][CH:36]([C:33]4[C:32]5[CH:42]=[CH:43][C:29]([F:28])=[CH:30][C:31]=5[O:35][N:34]=4)[CH2:41][CH2:40]3)=[O:11])=[CH:8][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 218397403,4-Dimethoxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid

Product 1

HCID 19886429HCID 19886429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.0 g of 4,5-dimethoxybenzocyclobutene-1-carboxylic acid (prepared according to the process described in Tetrahedron (1973) 29 p. 73) are dissolved in 130 ml of tetrahydrofuran, and 6.9 g of carbonyldiimidazole are added. The mixture is stirred at room temperature for 2 hours until the gaseous evolution has ceased. A solution of 8.5 g of 6-fluoro-3-piperid-4-yl-1,2-benzisoxazole in 100 ml of tetrahydrofuran is then added dropwise. The mixture is stirred at room temperature overnight. The expected product precipitates. It is filtered off and dried in a desiccator over phosphorus pentoxide.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customThe expected product precipitates
  3. filtrationIt is filtered off
  4. dry with materialdried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-2f957ec62a5d4860970598d93fe59811
Source dataset
uspto-grants-1992_07
Patent number
US05134147

Reaction notes

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