Water → (E)-2-cyano-3-(furan-2-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acrylamide

HRID 658653Notes

Reaction equation

[C:1]([CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][N:11]=1)=[O:5])#[N:2].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.O>CN(C=O)C>[C:1](/[C:3](=[CH:23]\[C:19]1[O:18][CH:22]=[CH:21][CH:20]=1)/[C:4]([NH:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][N:11]=1)=[O:5])#[N:2]

Participants

Conditions

Temperature: 150 °C

Procedure

312 mg of 2-cyano-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide and 150 uL of furan-2-carbaldehyde were mixed in 2.5 mL of DMF and heated in a microwave at 150° C. for 15 min. 5 ml of H2O was added and the resulting precipitate was collected and washed with water (4×) to give the crude product. Recrystallization from ethanol gave 180 mg of pure product as a brown solid. MS (M+H, 323); 1H NMR (400 MHz, DMSO-d6): δ, ppm: 6.82 (m, 1H)), 7.43 (d, 1H), 7.49 (m, 4H), 7.87 (m, 2H), 8.15 (s, 1H), 8.22 (br, s, 1H).

Workup

customthe resulting precipitate was collected
washwashed with water (4×)
customto give the crude product
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-0a6aee98e6be43caa9663768672074ae
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076491B2

Reaction notes

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