Methanethiol → HCID 14820158, compound

HRID 487083Notes

Reaction equation

HRID 487083 reaction equation
[C:1]([C:4]1[C:18]([OH:19])=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]([CH2:20]Cl)[CH:5]=1)(=[O:3])[CH3:2].[CH3:22][SH:23].C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:4]1[C:18]([OH:19])=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]([CH2:20][S:23][CH3:22])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 8471TriethylamineHCID 14820169HCID 14820169, compound

Product 1

HCID 14820158HCID 14820158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 600 mg of the compound from Example 127 was dissolved in 50 ml of methylene chloride and cooled to 0° C. Fifteen grams of methanethiol were added followed by the addition of 2 ml of triethylamine. The reaction was allowed to warm to room temperature and was stirred overnight. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and an acidic sodium choride solution. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography over silica gel eluting with 40% ethyl acetate in hexane providing 200 mg of the desired title product, m.p.=78° C.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography over silica gel eluting with 40% ethyl acetate in hexane providing 200 mg of the desired title product, m.p.=78° C.

Sources & evidence

ORD record
ord-4d5a69095e2847bb869267345f0901d3
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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