tert-Butyl mercaptan → HCID 10987855, compound

HRID 2188484Notes

Reaction equation

HRID 2188484 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].N12CCCN=C1CCCCC2>C(OCC)(=O)C>[C:12]([S:15][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 788712-(2-(2-Chloroethoxy)ethoxy)ethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 10987855HCID 10987855, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-[2-(2-chloroethoxy)ethoxy]ethanol (11.0 g, 65.24 mmol) and tert-butylthiol (7.35 mL, 65.23 mmol) cooled in an ice bath was slowly added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 9.75 mL, 65.23 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. This mixture was then diluted with ethyl acetate and filtered. The crude product in the filtrate was purified on a filter column eluted with ethyl acetate to give yellowish oil (14.4 g, 64.6 mmol, 99%): 1H NMR (300 MHz, CDCl3): d 3.73 (br s, 2H), 3.69-3.60 (m, 8H), 2.75 (t, J=7.4, 2H), 2.62 (br s, 1H), 1.32 (s, 9H); 13C NMR (75 MHz, CDCl3): d 72.47, 71.08, 70.33, 70.27, 61.71, 42.09, 30.95, 27.87; MS (ESI): m/e (M+1) Calcd. for C10H23O3S: 223, obsd.: 223.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. customThe crude product in the filtrate was purified on a filter column
  4. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-257b354a9cb04167a1bbed9778d20ab2
Source dataset
uspto-grants-2002_06
Patent number
US06410775B1

Reaction notes

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