Triethylamine → (5-((2-Mercapto-2-methylpropylthio)methyl)-1,3-phenylene)dimethanol

HRID 58007Notes

Reaction equation

HRID 58007 reaction equation
[SH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1.C(N(CC)CC)C.[CH3:20][C:21]1([CH3:24])[CH2:23][S:22]1>CO>[SH:22][C:21]([CH3:24])([CH3:23])[CH2:20][S:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1380502,2-DimethylthiiraneHCID 49780084(5-(Mercaptomethyl)-1,3-phenylene)dimethanol

Product 1

HCID 86671281(5-((2-Mercapto-2-methylpropylthio)methyl)-1,3-phenylene)dimethanolYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-(mercaptomethyl)-1,3-phenylene)dimethanol (0.163 g, 0.885 mmol) was dissolved in methanol (3 mL) in a small vial and a stir bar was added. To this solution was added triethylamine (0.016 mL, 0.118 mmol) followed by 2,2-dimethylthiirane (0.058 mL, 0.590 mmol) and the resulting mixture was capped and stirred overnight (16 hrs) at room temperature. The reaction was then concentrated, redissolved in dichloromethane, loaded onto a silica ptlc plate (1000 micron) and the plate was developed using 10% methanol in dichloromethane. The band corresponding to the product was scraped, filtered with neat ethyl acetate, and concentrated to give (5-((2-mercapto-2-methylpropylthio)methyl)-1,3-phenylene)dimethanol (0.095 g, 0.349 mmol, 59.1% yield). 1H NMR (400 Hz, CDCl3): δ 7.26 (s, 3H), 4.69 (s, 4H), 3.82 (s, 2H), 2.74 (s, 2H), 2.17 (s, 1H), 2.12 (br s, 2H), 1.43 (s, 6H); 13C NMR (400 Hz, CDCl3): δ 141.6, 138.9, 126.7, 124.3, 65.0, 49.0, 45.4, 38.4, 31.5; MS (m/z), expected: 272.4. found 295.0 (M+Na). See FIG. 30.

Workup

  1. additionwas added
  2. customthe resulting mixture was capped
  3. concentrationThe reaction was then concentrated
  4. dissolutionredissolved in dichloromethane
  5. filtrationfiltered with neat ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed2ecf89a6e947759dc99576b460348d
Source dataset
uspto-grants-2016_09
Patent number
US09434748B2

Reaction notes

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