4-Chloroaniline → HCID 15669323, compound

HRID 1464120Notes

Reaction equation

HRID 1464120 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[CH2:16]([O:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH3:17]>C1COCC1>[CH2:16]([O:18][C:19]1[S:20][C:21]([S:10]([NH:13][C:14]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:15])(=[O:12])=[O:11])=[CH:22][CH:23]=1)[CH3:17]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 70918Chlorosulfonyl isocyanateHCID 3398562-ethoxythiophene

Product 1

HCID 15669323HCID 15669323, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-chloroaniline (0.99 g, 7.8 mmole) in 30 ml of anhydrous THF at -78° C. under nitrogen was added chlorosulfonylisocyanate (1.09 g, 7.8 mmole). This mixture was stirred at -78° C. for 1 hr. 2-Ethoxythiophene (1 g, 7.8 mmole) was added, the ice bath was removed, and the reaction was stirred at room temperature for 2 hrs. The reaction was partially concentrated under vacuum, added to water and extracted with ethyl acetate. The organic layer was dried (sodium sulfate), filtered and concentrated under vacuum. The oil was chromatographed (4% methanol/methylene chloride) on silica gel. The desired fractions concentrated under vacuum and the resulting oil was dissolved in ethyl acetate (20 ml) and triturated with hexanes (450 ml) to provide 0.6 g of solid after drying under vacuum.

Workup

  1. customthe ice bath was removed
  2. stirringthe reaction was stirred at room temperature for 2 hrs
  3. concentrationThe reaction was partially concentrated under vacuum
  4. additionadded to water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe oil was chromatographed (4% methanol/methylene chloride) on silica gel
  10. concentrationThe desired fractions concentrated under vacuum
  11. dissolutionthe resulting oil was dissolved in ethyl acetate (20 ml)
  12. customtriturated with hexanes (450 ml)

Sources & evidence

ORD record
ord-fc0e81e5e5e94b6bbdbc68fab5f58949
Source dataset
uspto-grants-1994_04
Patent number
US05302724

Reaction notes

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