Hydrochloric Acid → HCID 13394284, compound

HRID 2164300Notes

Reaction equation

HRID 2164300 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[C:4]([NH2:17])[CH:3]=1.C(O[C:21](=[S:24])CC)C.[C:25]([O:29]Cl)(C)(C)[CH3:26].C(N(CC)CC)C.[ClH:38]>C(Cl)Cl>[Cl:38][C:16]1[CH:2]=[C:3]2[C:4](=[C:5]([C:6](=[O:7])[C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[CH:15]=1)[NH:17][C:25](=[O:29])[CH:26]2[S:24][CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetateHCID 223994921493244-95-3

Product 1

HCID 13394284HCID 13394284, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of 54.0 g (0.216 mole) of 4-chloro-4'-fluoro-2-aminobenzophenone in 700 ml of methylene chloride was cooled to -65° C. and 30.5 g (0.227 mol) of ethyl-2-methylthioacetate was added. Twenty six (26) g (0.227 mol) of 95% tertiary butoxy chloride was added dropwise under stirring over a 20 minute period while maintaining the temperature of the solution at -65° C. The resulting light brown yellow solution was stirred at -70° C. for one hour and 25 g (0.25 mol) of triethylamine was added to the solution. This mixture was allowed to warm to room temperature and 400 ml of 3N HCl was added to the mixture. The resulting mixture was heated at reflux temperature under vigorous stirring for 2 hrs. The resulting organic phase was separated, washed with 100 ml of water and dried. The methylene chloride was evaporated and the residue triturated with diethyloxide. The resulting solid was collected by filtration, washed and dried to give 35.1 g of product. The product was crystallized to give 31.1 g (43%) of the titled compound as off-white crystals, mp. 202°-204° C.

Workup

  1. stirringThe resulting light brown yellow solution was stirred at -70° C. for one hour
  2. temperatureto warm to room temperature
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux temperature
  5. stirringunder vigorous stirring for 2 hrs
  6. customThe resulting organic phase was separated
  7. washwashed with 100 ml of water
  8. customdried
  9. customThe methylene chloride was evaporated
  10. customthe residue triturated with diethyloxide
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-a9ae38d7963b4b9b9de629f3af03d609
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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