5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide → 5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid amide

HRID 1696757Notes

Reaction equation

C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[C:21]([CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[S:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:13][CH:12]=2)=[CH:19][CH:18]=1)#[N:22]

Participants

Conditions

Temperature: 50 °C

Procedure

5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide (260 mg) was suspended in TFA (10 mL) and stirred 2 h at 50° C. The mixture was evaporated to dryness and trituated with toluene (2 mL). The obtained precipitate was filtered off, washed with toluene and dried in vacuo to yield 5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid amide (157 mg, 73%) as a white solid.

Workup

customThe mixture was evaporated to dryness
filtrationThe obtained precipitate was filtered off
washwashed with toluene
customdried in vacuo

Sources & evidence

ORD record: ord-4b49f9f63d2c48edac2a20c8d2cfb593
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163778B2

Reaction notes

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