Triethylamine → HCID 59403792, compound

HRID 1255372Notes

Reaction equation

HRID 1255372 reaction equation
Cl.[SH:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[CH2:13]([CH:15]([CH2:19][CH2:20][CH2:21][CH3:22])[C:16](Cl)=[O:17])[CH3:14].[Cl-].[NH4+]>ClCCl>[SH:2][CH2:3][CH2:4][NH:5][C:16](=[O:17])[CH:15]([CH2:13][CH3:14])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 25517Ammonium ChlorideHCID 791032-Ethylhexanoyl chloride

Product 1

HCID 59403792HCID 59403792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

22.7 g of 2-mercaptoethylamine hydrochloride (0.2 mol) and 32.4 g of triethylamine (0.32 mol) were introduced in suspension in 130 ml of dichloromethane at 0° C.-5° C. Over the course of 25 minutes, 16.8 g of 2-ethylhexanoyl chloride (0.1 mol) were added dropwise. The batch was stirred at 0° C. to 5° C. for 1 hour, at 40° C. for 1.5 hours, and then at room temperature for 12 hours. 70 ml of saturated ammonium chloride solution were added and a phase separation was carried out. This was repeated twice and the organic phases were combined, dried over sodium sulfate, and freed of their solvent under reduced pressure. The residue obtained was purified by column chromatography (97 toluene:3 methanol).

Workup

  1. waitat room temperature for 12 hours
  2. customa phase separation
  3. dry with materialdried over sodium sulfate
  4. customThe residue obtained
  5. customwas purified by column chromatography (97 toluene:3 methanol)

Sources & evidence

ORD record
ord-119ec1ba758c4225907bdb84a474019c
Source dataset
uspto-grants-2013_06
Patent number
US08460445B2

Reaction notes

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