(+-)-Mercaptosuccinic acid → HCID 19600888, compound

HRID 609885Notes

Reaction equation

HRID 609885 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH2:18][CH2:19][CH2:20][CH2:21][OH:22].[C:23](O)(=[O:30])[CH:24]([CH2:26][C:27]([OH:29])=[O:28])[SH:25]>C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]2[N:18]([CH2:19][CH2:20][CH2:21][OH:22])[C:23](=[O:30])[CH:24]([CH2:26][C:27]([OH:29])=[O:28])[S:25]2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6268(+-)-Mercaptosuccinic acidHCID 90863-Amino-1-propanolHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 19600888HCID 19600888, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene (200 ml) were suspended 3,5-di-tert-butyl-4-hydroxybenzaldehyde (23.4 g) and 3-aminopropanol (9.01 g) under a nitrogen atmosphere. After fitting a Dean-Stark trap to the reactor, the suspension was refluxed for 2 hours. After allowing the mixture to cool, thiomalic acid (19.52 g) was added thereto, then the mixture was refluxed for an additional period of 3 hours. Benzene was removed by evaporation, and the resulting white solid was recrystallized from aqueous methanol to afford 10.5 g (25%) of the title compound as colorless crystals. mp 227-228° C. NMR (d6 -DMSO) (200 MHz) d: 1.37 (18H, s), 1.2-1.8 (2H, m), 2.3-2.8 (1H, m), 3.0-3.6 (5H, m), 4.0-4.2 (1H, m), 4.37 (1H, brs), 5.73 (1H, s), 7.10 (2H, s), 7.13 (1H, s)

Workup

  1. temperaturethe suspension was refluxed for 2 hours
  2. temperatureto cool
  3. temperaturethe mixture was refluxed for an additional period of 3 hours
  4. customBenzene was removed by evaporation
  5. customthe resulting white solid was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-ca56b10ee25f4d93b850b38c1d5c36e8
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

Loading…