Benzene → HCID 23345400, compound

HRID 1856489Notes

Reaction equation

HRID 1856489 reaction equation
Br[C:2]1[C:10]2[CH2:9][S:8](=O)(=O)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH2:13].[OH-:14].[NH4+:15].[CH:16]1C=CC=CC=1>N1C2C(=CC=CC=2)C=CC=1.C(OCC)C>[C:16]([C:2]1[C:10]2[CH2:9][S:8](=[O:14])(=[O:13])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:15]

Participants

7

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 14923Ammonium HydroxideHCID 23345398HCID 23345398, compound

Product 1

HCID 23345400HCID 23345400, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7047QuinolineSolvent2×

Procedure

4-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide (0.1 m) is dissolved in dry quinoline. To the quinoline solution is added (0.1 M) of cuprous cyanide. The temperature of the mixture is maintained between 100°-160° C. for about 6 to 12 hours. At the end of this time the mixture is poured into water and concentrated ammonium hydroxide. Benzene is added and the mixture is stirred until the solids are dissolved. Ethyl ether is added and the mixture is filtered to remove undissolved solids. The organic and aqueous phases are separated and the aqueous phase is discarded. The organic phase is then washed with 6 N ammonium hydroxide, 6 N hydrochloric acid and saturated sodium chloride. Removal of the benzene-ethyl ether gives the title compound which is used without further purification.

Workup

  1. temperatureThe temperature of the mixture is maintained between 100°-160° C. for about 6 to 12 hours
  2. dissolutionare dissolved
  3. filtrationthe mixture is filtered
  4. customto remove undissolved solids
  5. customThe organic and aqueous phases are separated
  6. washThe organic phase is then washed with 6 N ammonium hydroxide, 6 N hydrochloric acid and saturated sodium chloride
  7. customRemoval of the benzene-ethyl ether

Sources & evidence

ORD record
ord-92467ac163fc4971bd3d88e8a64a9868
Source dataset
uspto-grants-1980_08
Patent number
US04219648

Reaction notes

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