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Cysteamine Hydrochloride → HCID 22253943, compound

HRID 515951
Notes
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Reaction equation

HRID 515951 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[C:6]([Cl:12])(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]>>[ClH:12].[CH3:8][C:7]([CH3:10])([CH3:9])[C:6](=[O:11])[S:5][CH2:4][CH2:3][NH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 62493Pivaloyl chloride

Product 1

HCID 22253943HCID 22253943, compoundYield 94%

Procedure

A solution of cysteamine hydrochloride (30.81 mmol) in pivaloyl chloride (10 mL) was heated to 100° C. during 15 minutes. The reaction mixture was allowed to cool down to room temperature and was triturated in Et2O. The mixture was filtered. The solid was washed with Et2O and then dissolved in DMF (50 mL and 5 drops of HCl) upon heating. After cooled down to room temperature, the mixture was precipitated with Et2O, filtered and washed with Et2O to give after drying under vacuum the expected compound as a white solid in 94% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.19 (s, 9H), 2.88 (t, J=7.08 Hz, 2H), 3.05-3.08 (m, 2H), 8.30 (s, 3H).

Workup

  1. customwas triturated in Et2O
  2. filtrationThe mixture was filtered
wash
The solid was washed with Et2O
  • dissolutiondissolved in DMF (50 mL and 5 drops of HCl)
  • temperatureupon heating
  • temperatureAfter cooled down to room temperature
  • customthe mixture was precipitated with Et2O
  • filtrationfiltered
  • washwashed with Et2O
  • customto give
  • dry with materialafter drying under vacuum the expected compound as a white solid in 94% yield
  • Sources & evidence

    ORD record
    ord-4dadf182d78d4490bd7b5fb27108eeac
    Source dataset
    uspto-grants-2015_08
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US09109001B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes