Water → HCID 12909817, compound

HRID 2418335Notes

Reaction equation

HRID 2418335 reaction equation
ClCl.CC[C:5](OCC)=[S:6].[O:10]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N([CH2:29][CH3:30])CC)C.[OH2:31]>C(Cl)Cl>[O:31]=[C:30]1[CH:29]([S:6][CH3:5])[C:20]2[C:18](=[C:17]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:23]=[CH:22][CH:21]=2)[NH:19]1

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 24526ChlorineHCID 75899Benzenamine, 2-phenoxy-HCID 12284386Ethyl methylthioacetate

Product 1

HCID 12909817HCID 12909817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
60 °C

Procedure

Chlorine gas (3.1 g.) was absorved into dried methylene chloride (70 ml.) under cooling. To the solution was added dropwise a solution of ethyl methylthioacetate (6.35 g.) in methylene chloride (10 ml.) over 30 minutes under stirring at 31 60° C. and stirred for 10 minutes at the same temperature. A solution of 2-phenoxyaniline (17.5 g.) in methylene chloride (10 ml.) was added dropwise to the mixture over 30 minutes at -65° C. and stirred at the same temperature for an hour. A solution of triethylamine (7.5 g.) in methylene chloride (10 ml.) was added dropwise over 15 minutes at -65° C. and stirred for 30 minutes at the same temperature. The reaction mixture was allowed to stand at ambient temperature, and water (40 ml.) was added and stirred for 10 minutes. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue was subjected to column chromatography on silica gel (400 g.) and eluted with a mixture of benzene and n-hexane (1:1), benzene and ethyl acetate successively. The ethyl acetate eluate was concentrated and the powdery residue was recrystallized from a mixture of benzene and n-hexane to give white needles of the captioned compound (6.25 g.). mp 149° to 150° C.

Workup

  1. temperatureunder cooling
  2. stirringstirred for 10 minutes at the same temperature
  3. stirringstirred at the same temperature for an hour
  4. stirringstirred for 30 minutes at the same temperature
  5. customto stand at ambient temperature
  6. stirringstirred for 10 minutes
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. washeluted with a mixture of benzene and n-hexane (1:1), benzene and ethyl acetate successively
  11. concentrationThe ethyl acetate eluate was concentrated
  12. customthe powdery residue was recrystallized from a mixture of benzene and n-hexane
  13. customto give white needles of the captioned compound (6.25 g.)

Sources & evidence

ORD record
ord-59e09966e5ee449ab4aa824b58392e73
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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