Phosphoric Acid → HCID 54012132, compound

HRID 1289885Notes

Reaction equation

HRID 1289885 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10]([CH2:20][CH2:21][OH:22])=[C:11]([CH3:19])[NH:12]3)=[O:7])=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.OP(O)(O)=O.C(OCC)C>CS(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10]([CH2:20][CH:21]=[O:22])=[C:11]([CH3:19])[NH:12]3)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 54487831HCID 54487831, compound

Product 1

HCID 54012132HCID 54012132, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture in dry DMSO (11.6 mL) of 2-(4-chlorobenzoyl-5-methoxy-2-methylindol-3-yl) ethanol (2.0 g, 5.8 mmol), prepared as in step 1, and dicyclohexylcarbodiimide (DCC) (1.6 g. 7.8 mmol) was added 1.0 M H3PO4 in DMSO (1.0 mL) and the reaction mixture was stirred at room temperature for 48 hours. Diethyl ether (100 mL) was added and the solid dicyclohexylurea byproduct was removed by filtration. The filtrate was washed with water, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was triturated with hexane/ether to give 1.9 g (95%) of (4-chlorobenzoyl-5-methoxy-2-methylindol-3-yl) acetaldehyde.

Workup

  1. customthe solid dicyclohexylurea byproduct was removed by filtration
  2. washThe filtrate was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was triturated with hexane/ether

Sources & evidence

ORD record
ord-b17ca7978a19489a8535ded6ce994a1b
Source dataset
uspto-grants-1998_05
Patent number
US05750558

Reaction notes

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