Dimethyl Sulfide → HCID 131716950, compound

HRID 1086795Notes

Reaction equation

HRID 1086795 reaction equation
CSC.[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([CH3:19])[CH:13]=1>>[CH:16]1[C:17]([OH:18])=[CH:12][CH:13]=[C:14]([CH3:19])[CH:15]=1.[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 2879P-CresolHCID 78114-Methylbenzenethiol

Product 1

HCID 131716950HCID 131716950, compound

Procedure

The dried resin peptide (1 g) was premixed with dimethylsulfide, p-thiocresol, and p-cresol; liquid HF at -78° C. was then added to give approximately a final volume of 10 mL (65:2.5:7.5:25 by volume). The mixture was equilibrated to 0° C. by stirring in an ice bath. After 2 hr, the HF and dimethyl sulfide were removed in vacuo. The high HF treatment was initiated by recharging the reaction vessel at -78° C. with about 14 mL of fresh HF to give a total volume of 15 mL HF-p-cresol-p-thiocresol. The reaction was carried out at 0° for 1 hr. After evaporation of HF at 0° C. and washing with cold ether, the crude reaction mixture was extracted with 10% aqueous acetic acid. The mixture was then lyophilized to dryness.

Workup

  1. additionliquid HF at -78° C. was then added
  2. customto give approximately a final volume of 10 mL (65:2.5:7.5:25 by volume)
  3. customwas equilibrated to 0° C.
  4. customthe HF and dimethyl sulfide were removed in vacuo
  5. customat -78° C.

Sources & evidence

ORD record
ord-09308f9a61c84bb89600030e3a4d00fc
Source dataset
uspto-grants-1991_07
Patent number
US05032576

Reaction notes

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