Acetic Acid → HCID 21886036, compound

HRID 723231Notes

Reaction equation

[CH3:1][S-:2].[Na+].[Br:4][C:5]1[CH:6]=[C:7]([S:11]([C:14]2[CH:15]=[C:16]([C:22]#[N:23])[S:17][C:18]=2[N+]([O-])=O)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.C(O)(=O)C>CCO.C1COCC1.C(OCC)C>[Br:4][C:5]1[CH:6]=[C:7]([S:11]([C:14]2[CH:15]=[C:16]([C:22]#[N:23])[S:17][C:18]=2[S:2][CH3:1])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of sodium thiomethoxide (1.87 g, 26.8 mmol) in EtOH (26.8 mL, anhydrous) was added to a suspension of 4-(3-bromo-benzenesulfonyl)-5-nitro-thiophene-2-carbonitrile (10 g, 26.8 mmol, Example 286: step e) in THF (67 mL, anhydrous) portionwise at −78° C. The temperature of the reaction was maintained at −78° C. with stirring for 1 hour. The reaction was quenched with acetic acid (2 mL, 34.9 mmol) at −78° C. followed by warming the reaction mixture to rt and then filtered. The yellow solids were washed with diethyl ether and saved. The filtrate was concentrated in vacuo resulting in a residue that was suspended in diethyl ether and stirred at rt overnight. The solids were filtered from the suspension. The combined yellow solids were dried under high vacuum to afford the title compound (8.77 g, 87.4%). 1H-NMR (DMSO-d6): δ 8.45 (s, 1H), 7.97–8.16 (m, 3H), 7.62–7.67 (m, 1H), 2.71 (s, 3H).

Workup

temperatureby warming the reaction mixture to rt
filtrationfiltered
washThe yellow solids were washed with diethyl ether
concentrationThe filtrate was concentrated in vacuo
customresulting in a residue that
stirringstirred at rt overnight
filtrationThe solids were filtered from the suspension
customThe combined yellow solids were dried under high vacuum

Sources & evidence

ORD record: ord-46533a896e1f4de7b94515979ce6fd0b
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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