Chlorotrimethylsilane → Propanoyloxymethyl 4-Chlorophenylcarbamate

HRID 1609749Notes

Reaction equation

HRID 1609749 reaction equation
[Si](Cl)(C)(C)C.[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[C:14](Cl)(=[O:22])[O:15][CH2:16][O:17][C:18](=[O:21])[CH2:19][CH3:20]>CCOCC>[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:14](=[O:22])[O:15][CH2:16][O:17][C:18](=[O:21])[CH2:19][CH3:20])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 78124-ChloroanilineHCID 14800977Propanoyloxymethyl Carbonochloridate

Product 1

HCID 14800992Propanoyloxymethyl 4-ChlorophenylcarbamateYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Me3SiCl (2.3 mL, 18 mmol) is added to 4-chloroaniline (4.6 g, 36 mmol) in Et2O (50 mL) at room temperature with stirring during 20 min. Following an additional 30 min Stirring 7c (4.05 g, purity 90%, 22 mmol) in Et2O (30 mL) is slowly (1 h) added. The stirring is continued overnight. The precipitate is filtered off and the filtrate extracted with ice-cold 0.1N HCl (50 mL), H2O (3×50 mL), dried (MgSO4) and evaporated. The residue (4.9 g) is extracted with hexane (50 mL) to leave 3.3 g (71%) of the title compound, mp 90°-91° C.

Workup

  1. waitFollowing an additional 30 min
  2. custom(1 h)
  3. additionadded
  4. waitThe stirring is continued overnight
  5. filtrationThe precipitate is filtered off
  6. extractionthe filtrate extracted with ice-cold 0.1N HCl (50 mL), H2O (3×50 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. extractionThe residue (4.9 g) is extracted with hexane (50 mL)

Sources & evidence

ORD record
ord-c47fdb1b93c74303910c38b7f1cda87d
Source dataset
uspto-grants-1995_03
Patent number
US05401868

Reaction notes

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