Benzoic Acid → HCID 67801498, compound

HRID 1379613Notes

Reaction equation

HRID 1379613 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:35]1([CH2:41][C:42]2[CH:43]=[C:44]([CH:58]=[CH:59][CH:60]=2)[O:45][CH2:46]/[CH:47]=[CH:48]\[CH2:49][NH:50][C:51](=[O:57])[CH2:52][S:53][CH2:54][CH2:55][NH2:56])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>ClCCl>[N:35]1([CH2:41][C:42]2[CH:43]=[C:44]([CH:58]=[CH:59][CH:60]=2)[O:45][CH2:46]/[CH:47]=[CH:48]\[CH2:49][NH:50][C:51](=[O:57])[CH2:52][S:53][CH2:54][CH2:55][NH:56][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 67649208HCID 67649208, compound

Product 1

HCID 67801498HCID 67801498, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was dissolved 0.97 g (0.008 mol) of benzoic acid in 60 ml of dichloromethane and added 1.22 g (0.008 mol) of HOBt and 1.65 g (0.0095 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 3.0 g (0.008 mol) of N-[4-[3-(piperidinomethyl) phenoxy]-cis-2-butenyl]-2-(2-aminoethylthio)acetamide and the mixture was stirred for 18 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with 5% aqueous solution of sodium hydroxide and with water and dried over Glauber's salt. Then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=5:1) to give 0.9 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 18 hours at room temperature
  4. filtrationThe precipitate was filtrated off
  5. washthe filtrate was washed with 5% aqueous solution of sodium hydroxide and with water
  6. dry with materialdried over Glauber's salt
  7. customThen the solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-f1d5fa29672945fb804e41b945f7d150
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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