Propionic Acid → HCID 18974812, compound

HRID 964713Notes

Reaction equation

HRID 964713 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:6]([CH:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)O)[CH:7]=1.[SH:26][CH:27]([CH2:31][C:32]([OH:34])=[O:33])[C:28](O)=[O:29].C(O)(=O)CC>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:20]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:28](=[O:29])[CH:27]([CH2:31][C:32]([OH:34])=[O:33])[S:26][CH:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 6268(+-)-Mercaptosuccinic acidHCID 19077420HCID 19077420, compound

Product 1

HCID 18974812HCID 18974812, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A stirred mixture of 50.0 g (141 mmol) of (5-chloro-2-neopentylamino-phenyl)-naphthalen-1-yl-methanol, 27.58 g (184 mmol, 1.3 equivalents) of mercaptosuccinic acid, and 340 mL of propionic acid was heated to 130° C. with a nitrogen purge. After 48 hours, the reaction mixture was cooled to room temperature giving a precipitate, treated with 200 mL of water, cooled to -5° C. with stirring, and filtered giving 60.83 g (92% yield) of the title compound as an off white solid.

Workup

  1. custompurge
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customgiving a precipitate
  4. temperaturecooled to -5° C.
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e8c72af577174f5da2fc5928306670b8
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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