Dimethylformamide → HCID 9990935, compound

HRID 565594Notes

Reaction equation

HRID 565594 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[O:7][C:6]=2[CH:15]=1.[Cu][C:17]#[N:18].[CH3:19][N:20](C=O)C>>[C:19]([C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:17]#[N:18])=[CH:13][C:8]=3[O:7][C:6]=2[CH:15]=1)#[N:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 5263563,7-Dibromodibenzo[b,d]furanHCID 178418546HCID 178418546, compound

Product 1

HCID 9990935HCID 9990935, compoundYield 97.43%

Procedure

A suspension of 3,7-dibromo-dibenzofuran (18, 10.27 g, 31.51 mmol) and copper(I) cyanide (8.23 g, 94.5 mmol) in DMF (80 mL) was refluxed under N2 for 6 h. The reaction mixture was poured into ice-water (300 mL). The precipitated solid was collected and stirred for 5 h in a solution of ethylenediamine (50 mL) in water (300 mL). The solid was filtered off, washed with water, then stirred in 10% sodium cyanide solution (100 mL) for 4 h. The solid was further purified by suspension in hot ethanol (100 mL) to give a pale yellow powder (6.69 g, 97.43%): mp 322-325° C. (dec.); HPLC method 3 tR=16.56 min (96.6 area %); 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, J=8.3 Hz, 2 H), 8.48 (s, 2 H), 7.95 (dd, J1=8.3 Hz, J2=1.0 Hz, 2 H); EI-MS m/z 218 (M+). Anal. (C14H6N2.0.23H2O) C, H, N.

Workup

  1. temperaturewas refluxed under N2 for 6 h
  2. customThe precipitated solid was collected
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. stirringstirred in 10% sodium cyanide solution (100 mL) for 4 h
  6. customThe solid was further purified by suspension in hot ethanol (100 mL)

Sources & evidence

ORD record
ord-13e96e0d62eb4735b00da7ce969f81ed
Source dataset
uspto-grants-2001_01
Patent number
US06172104B2

Reaction notes

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