Dicyclohexylcarbodiimide → HCID 23131681, compound

HRID 1669352Notes

Reaction equation

HRID 1669352 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])=[O:2].[CH3:12][S:13]([NH2:16])(=[O:15])=[O:14].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.ClCCl>[CH3:12][S:13]([NH:16][C:6]([C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:1]=[O:2])=[O:7])(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 120773-CarboxybenzaldehydeHCID 218852-DimethylaminopyridineHCID 72879Methanesulfonamide

Product 1

HCID 23131681HCID 23131681, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.18 g of 3-formylbenzoic acid, 6.99 g of methanesulfonamide, 200 ml of dichloromethane, 8.95 g of dimethylaminopyridine, 15.22 g of dicyclohexylcarbodiimide and 100 ml of tetrahydrofuran was stirred at room temperature. The reaction solution was concentrated under reduced pressure, dissolved in ethyl acetate, a 1 N aqueous sodium hydroxide solution was added, and the layers were separated. To the aqueous layer was added 2 N hydrochloric acid to adjust to pH 1, this was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then concentrated to obtain 4.01 g of 3-[(methanesulfonyl)aminocarbonyl]benzaldehyde [Compound No. (j)] as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. additiona 1 N aqueous sodium hydroxide solution was added
  4. customthe layers were separated
  5. additionTo the aqueous layer was added 2 N hydrochloric acid
  6. extractionthis was extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bb131e9173b14dc9ae0bceb574002926
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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