Bromonitromethane → HCID 19800065, compound

HRID 1646884Notes

Reaction equation

HRID 1646884 reaction equation
Cl[C:2]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:3]=1[C:4]#[N:5].[SH:12]CCC#N.Br[CH2:18][N+:19]([O-:21])=[O:20]>CN(C=O)C>[NH2:5][C:4]1[C:3]2[CH:6]=[C:7]([Cl:11])[CH:8]=[C:9]([Cl:10])[C:2]=2[S:12][C:18]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 68423BromonitromethaneHCID 70477Propanenitrile, 3-mercapto-HCID 198000612,3,5-Trichlorobenzonitrile

Product 1

HCID 19800065HCID 19800065, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,3,5-Trichlorobenzonitrile (9.7 g, 47 mmol) and 3-mercaptopropionitrile (4.9 g, 56 mmol) (L. Bauer, T.L. Welsh, J. Org. Chem., 1443 (1961)) was dissolved in 130 ml of DMF. The mixture was stirred and cooled to 0° C., flushed with a stream of nitrogen, and 25% potassium hydroxide (20 ml) was added dropwise. When the addition was complete the mixture was stirred for 0.5 h and bromonitromethane (3.92 ml, 56 mmol) was added dropwise. The ice bath was removed and the mixture was stirred for a further 16 h. The mixture was poured into ice-water and the precipitate was isolated, washed with water and dried to afford 10.6 g (86%) of 3-amino-5,7-dichloro-2-nitrobenzo[b]-thiophene M.p. 290°-92° C. 1H-NMR (DMSO-d6): 8.02 (d, 1H), 8.54 (d, 1H), 9.00 (br. s, 1H).

Workup

  1. customflushed with a stream of nitrogen, and 25% potassium hydroxide (20 ml)
  2. additionwas added dropwise
  3. additionWhen the addition
  4. stirringwas stirred for 0.5 h
  5. customThe ice bath was removed
  6. stirringthe mixture was stirred for a further 16 h
  7. additionThe mixture was poured into ice-water
  8. customthe precipitate was isolated
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-55112057ab924f068a8a82c26bf07ee3
Source dataset
uspto-grants-1993_01
Patent number
US05182279

Reaction notes

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