Sodium Chloride → HCID 67799970, compound

HRID 1379619Notes

Reaction equation

HRID 1379619 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=2)[O:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][NH:16][C:17](=[O:23])[CH2:18][S:19][CH2:20][CH2:21][NH2:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:27]([O:29][C:30](Cl)=[O:31])[CH3:28].[Cl-].[Na+]>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=2)[O:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][NH:16][C:17](=[O:23])[CH2:18][S:19][CH2:20][CH2:21][NH:22][C:30]([O:29][CH2:27][CH3:28])=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 67649208HCID 67649208, compound

Product 1

HCID 67799970HCID 67799970, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

There was dissolved 2.7 g (0.0072 mol) of N-[4-[3-(piperidinomethyl)phenoxy]-cis-2-butenyl]-2(2-aminoethylthio)acetamide in 20 ml of pyridine and added dropwise 0.78 g (0.0072 mol) of ethylchlorocarbonate under cooling with ice, and the mixture was stirred for 18 hours at room temperature. The obtained reaction mixture was poured into ice water and saturated with sodium chloride. The deposited oily matter was extracted with chloroform and washed with saturated aqueous solution of sodium chloride, and then dried over Glauber's salt. Then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 0.8 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. customThe obtained reaction mixture
  3. extractionThe deposited oily matter was extracted with chloroform
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over Glauber's salt
  6. customThen the solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9a8a872faf704239b969a0eef0bf3019
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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