Tetrahydrofuran → HCID 54530116, compound

HRID 1440445Notes

Reaction equation

HRID 1440445 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:4][CH:3]=1.O[CH2:15][NH:16][C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O1CCCC1>Cl.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([NH:13][CH2:15][NH:16][C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 76896Octadecanamide, N-(hydroxymethyl)-HCID 18983658HCID 18983658, compound

Product 1

HCID 54530116HCID 54530116, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 200-ml flask equipped with a stirrer and a condenser were charged 8.0 g of 3-(p-hydroxyphenylthio)propanamide, 10.6 g of N-hydroxymethyl-n-octadecanamide, 5 drops of concentrated hydrochloric acid and 120 ml of tetrahydrofuran, and stirred with heating at 60° C. for 5 hours. The reaction mixture was cooled to room temperature and then poured into 300 ml of distilled water. The white crystals precipitated were collected by filtration and recrystallized from isopropanol to obtain 12.0 g of the desired compound. Melting point: 172° C.

Workup

  1. customInto a 200-ml flask equipped with a stirrer and a condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe white crystals precipitated
  4. filtrationwere collected by filtration
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-a26331b78fe247e3954320d5f10c9b8c
Source dataset
uspto-grants-1996_03
Patent number
US05498772

Reaction notes

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