Acetyl chloride → HCID 178477169, compound

HRID 2111445Notes

Reaction equation

HRID 2111445 reaction equation
C[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[S:7])=[CH:4][CH:3]=1.[C:10](Cl)(=[O:12])[CH3:11]>>[C:10]([SH:7]=[CH:6][C:5]1[CH:4]=[CH:3][CH:2]=[CH:9][CH:8]=1)(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 181775354-Methylthiobenzaldehyde

Product 1

HCID 178477169HCID 178477169, compound

Procedure

Two other S-protected p-thiobenzaldehydes were obtained as shown in Scheme 2 (FIG. 15). The thiocyanato-benzaldehyde 8 was prepared according to a general procedure (Suzuki and Abe (1996) Synth. Commun., 26: 3413-3419) in 20% yield. All attempts to improve the yield by replacement of DMF with 1,3-dimethyl-2-imidazolidinone, increasing the temperature, or prolonging the reaction time were unsuccessful. S-Acetylthiobenzaldehyde 9 was prepared in a two-step one-flask procedure. Cleavage of the methyl group of 4-methylthiobenzaldehyde according to a general procedure (Tiecco et al. (1982) Synthesis, 478-480) followed by trapping of the resulting anion with acetyl chloride afforded the desired S-acetylthiobenzaldehyde 9 in 55% yield.

Workup

  1. temperatureincreasing the temperature
  2. customS-Acetylthiobenzaldehyde 9 was prepared in a two-step one-flask procedure

Sources & evidence

ORD record
ord-faeb84eeefc64c9fb7da96270a2c87da
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

Loading…