Bromonitromethane → HCID 19800043, compound

HRID 1646883Notes

Reaction equation

HRID 1646883 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+]([O-])=O)[CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2:22].[Na+].[Na+].Br[CH2:26][N+:27]([O-:29])=[O:28]>CN(C=O)C.O>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][C:4]=2[S:22][C:26]=1[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 68423BromonitromethaneHCID 73972Sodium sulfide nonahydrateHCID 969244-Chloro-2-nitrobenzonitrile

Product 1

HCID 19800043HCID 19800043, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-2-nitrobenzonitrile (2.19 g, 12 mmol) (EP 110,559; cf. Chem. Abstr., 101 130431 f (1984)) in 40 ml of DMF was stirred under cooling (ice bath), and a solution of sodium sulfide nonahydrate (3.47 g, 14.4 mmol) in 8 ml of water was added dropwise. When the addition was complete (0.5 h) the mixture was stirred for 15 min. and bromonitromethane (2.02 g, 14.4 mmol) was added dropwise. The ice bath was removed and stirring was continued for 16 h. The reaction mixture was poured into icewater and the yellow precipitate was filtered off and dried to afford 1.05 g (38%) of 3-amino-6-chloro-2-nitrobenzo[b]thiophene M.p. 243°-245° C. 1H-NMR (DMSO-d67): δ 7.55 (dd, 1H), 8.11 (d, 1H), 8.36 (d, 1H), 8.97 (br. s, 2H).

Workup

  1. temperatureunder cooling (ice bath)
  2. additionWhen the addition
  3. custom(0.5 h)
  4. customThe ice bath was removed
  5. stirringstirring
  6. waitwas continued for 16 h
  7. additionThe reaction mixture was poured into icewater
  8. filtrationthe yellow precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-4feff9b0231c4ae5970edc27e1138ff3
Source dataset
uspto-grants-1993_01
Patent number
US05182279

Reaction notes

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