4-Toluenesulfonyl chloride → 3-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate

HRID 1374083Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>CC#N>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) solution of 4-[(3-hydroxypropyl)amino]benzonitrile (from step (i) above; 17 g, 96.5 mmol) in dry MeCN (195 mL) was treated with triethylamine (9.8 g, 96.5 mmol) and then p-toluenesulfonyl chloride (20.2 g, 106 mmol). The mixture was stirred at 0° C. for 90 minutes before being concentrated in vacuo. Water (200 mL) was added to the residue, and the aqueous solution was extracted with DCM. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by crystallisation from iso-propanol to yield 24.6 g (77%) of the sub-title compound.

Workup

concentrationbefore being concentrated in vacuo
additionWater (200 mL) was added to the residue
extractionthe aqueous solution was extracted with DCM
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by crystallisation from iso-propanol

Sources & evidence

ORD record: ord-be508c8ac20143f980b5d144828f87f8
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07164017B2

Reaction notes

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