Dimethylformamide → HCID 23156962, compound

HRID 2110108Notes

Reaction equation

HRID 2110108 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[O:8][C:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[CH3:20][N:21](C=O)C>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([C:9]2[O:8][C:7]([C:5]3[O:6][C:2]([C:20]#[N:21])=[CH:3][CH:4]=3)=[CH:11][CH:10]=2)=[CH:13][CH:14]=1)#[N:17]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 23156960HCID 23156960, compound

Product 1

HCID 23156962HCID 23156962, compoundYield 40%

Procedure

A mixture of 4 (740 mg, 2.35 mmol) and Cu(I)CN (423 mg, 4.7 mmol) in dry DMF (25 mL) was refluxed for 48 h. The reaction mixture was poured onto water/ammonia and extracted with methylene chloride. The extract was washed with water and brine, dried over Na2SO4, then passed on silica gel to give analytically pure product 5 in 40% yield, mp 194-195° C. 1H NMR (DMSO-d6); δ 7.17 (d, J=3.6 Hz, 1H), 7.21 (d, J=3.6 Hz, 1H), 7.43 (d, J=3.6 Hz, 1H), 7.76 (d, J=3.6 Hz, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.99 (d, J=8.4 Hz, 2H). 13C NMR (DMSO-d6); δ 152.3, 149.3, 144.3, 133.0, 132.9, 125.6, 124.3, 124.1, 118.7, 112.0, 111.8, 111.5, 110.0, 107.9. EIMS (m/z, rel.int.); 260 (M+, 100), 231 (15), 203 (25), 177 (25), 140 (10), 130 (55). Calcd for C16H8N2O2: C, 73.84; H, 3.09; N, 10.76. Found. C, 73.62; H, 3.18; N, 10.92.

Workup

  1. temperaturewas refluxed for 48 h
  2. additionThe reaction mixture was poured onto water/ammonia
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water and brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-1edd08049c854fd2afb58b8aa9477d07
Source dataset
uspto-grants-2009_04
Patent number
US07517893B2

Reaction notes

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