4-Toluenesulfonyl chloride → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

HRID 565411

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C(N(CC)CC)C>[S:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

Conditions

Temperature: 95 °C

Procedure

To a 25 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (4.5 mmol) in 10 mL of triethylamine was added 1.3 g (6.7 mmol) of tosyl chloride. The reaction mixture was heated to 95° C. for 4 h. The reaction mixture was quenched by pouring into 10 mL of ice water and filtered. The solid was washed with water (3×10 mL), triterated with ether (25 mL), and dried in vacuo to give N-tosyl-indole-3-carboxaldehyde (85-90% yield).

Workup

customThe reaction mixture was quenched
additionby pouring into 10 mL of ice water
filtrationfiltered
washThe solid was washed with water (3×10 mL), triterated with ether (25 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-57a794a6f41442d4bfd300e90dc784e7
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172084B2

Linked notes

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