Propyl chloroformate → HCID 68124991, compound

HRID 441270Notes

Reaction equation

HRID 441270 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH3:7])=[O:3].[NH2:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[NH:12][C:13](=[O:19])/[CH:14]=[C:15](\[O:17][CH3:18])/[CH3:16].O1CCCC1>C(N(CC)CC)C>[CH2:5]([O:4][C:2]([NH:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[NH:12][C:13](=[O:19])/[CH:14]=[C:15](\[O:17][CH3:18])/[CH3:16])=[O:3])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 7998Propyl chloroformateHCID 8028TetrahydrofuranHCID 68125287HCID 68125287, compound

Product 1

HCID 68124991HCID 68124991, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

27 g of propyl chloroformate were slowly added to a mixture of 41.2 g of m-amino-3-methoxy-crotonanilide, 300 ml of tetrahydrofuran and 22.2 g of triethylamine and the mixture was stirred for 16 hours at 20° C. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8- 2 methylene chloride-acetone mixture to obtain 40 g of m-(n-propyloxycarbonylamino)-3-methoxy-crotonanilide melting at 115° C. Crystallization from chloroform did not change the melting point.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed over silica gel
  4. washwas eluted with an 8- 2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-6c93fe0107be4b5689fb9b0709e06773
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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