Ethanol → HCID 135618202, compound

HRID 1817195Notes

Reaction equation

HRID 1817195 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[SH:10])[C:5]#[N:6].[CH2:11]([OH:13])[CH3:12]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[NH:6])[O:13][CH2:11][CH3:12])[CH:7]=[CH:8][C:9]=1[SH:10]

Participants

5

Reactant 2

HCID 702EthanolHCID 200371753-Bromo-4-mercaptobenzonitrile

Product 1

HCID 135618202HCID 135618202, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

3-Bromo-4-mercaptobenzonitrile (10 g) was dissolved in toluene (50 ml) and chloroform (80 ml), followed by adding thereto ethanol (3.0 ml), and the resulting mixture was cooled to −10° C. Hydrochloric acid gas was bubbled into the mixture through a bubbler for 10 minutes and the resulting mixture was stirred at the same temperature for 30 minutes. The reaction mixture was allowed to stand in a refrigerator for 60 hours and then the completion of the reaction was confirmed by HPLC(ODS-A212). Dry nitrogen was bubbled into the reaction solution through a bubbler for 20 minutes and the hydrochloric acid gas was distilled off. The precipitate was collected by filtration, washed with toluene/chloroform and then dried to obtain ethyl 3-bromo-4-mercaptobenzene-carboximidate (13.6 g) as a light-yellow solid.

Workup

  1. additionby adding
  2. customHydrochloric acid gas was bubbled into the mixture through a bubbler for 10 minutes
  3. waitto stand in a refrigerator for 60 hours
  4. customDry nitrogen was bubbled into the reaction solution through a bubbler for 20 minutes
  5. distillationthe hydrochloric acid gas was distilled off
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with toluene/chloroform
  8. customdried

Sources & evidence

ORD record
ord-f4304f86af634b388089b801fd0df690
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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