Pyridine → HCID 1714278, compound

HRID 1028926Notes

Reaction equation

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>O>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:6][C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=2[O:8][CH3:9])[CH:2]=[O:1])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 3-hydroxy-4-methoxybenzaldehyde 12 (5.0 g, 32 mmol) and p-toluenesulfonyl chloride (10.0 g, 52.5 mmol) was dissolved in pyridine (12.5 mL, 154 mmol). The reaction mixture stirred for 5 min and maintained at 70-80° C. The clear reaction mixture becomes turbid and becomes slurry. The stirring was continued for a period of 2 h at 70-80° C. The reaction completion was determined by TLC and the contents of the flask were cooled to room temperature and poured in to cold water. The white crystalline solid formed was filtered, washed successively with 5 mL 1:1 HCl:H2O, 5 mL of 5% NaOH solution and water till the filtrate is free from pyridine, dried to constant weight to get the desired product 21. Yield: 98%; white solid mp 148-151° C. 1H NMR: δ 2.40 (s, 3H, CH3), 3.71 (S, 3H, OCH3), 6.91-7.83 (m, 7H, Ar—H), 9.83 (s, 1H, CHO). Anal. Calcd for C15H14O5S: C, 58.81, H, 4.61. Found: C, 58.79, H, 4.59.

Workup

waitThe stirring was continued for a period of 2 h at 70-80° C
temperaturethe contents of the flask were cooled to room temperature
customThe white crystalline solid formed
filtrationwas filtered
washwashed successively with 5 mL 1:1 HCl
customdried to constant weight

Sources & evidence

ORD record: ord-637682677a8b48a789707d5e2393ae14
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735620B2

Reaction notes

Loading…