Tetrahydrofuran → HCID 68125732, compound

HRID 441271Notes

Reaction equation

HRID 441271 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3].[NH2:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[NH:13][C:14](=[O:20])/[CH:15]=[C:16](\[O:18][CH3:19])/[CH3:17].O1CCCC1>C(N(CC)CC)C>[CH2:5]([O:4][C:2]([NH:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[NH:13][C:14](=[O:20])/[CH:15]=[C:16](\[O:18][CH3:19])/[CH3:17])=[O:3])[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 61140Butyl chloroformateHCID 68125287HCID 68125287, compound

Product 1

HCID 68125732HCID 68125732, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

12 g of n-butyl chloroformate were slowly added to a mixture of 16.5 g of m-amino-3-methoxy-crotonanilide, 320 ml of tetrahydrofuran and 8.9 g of triethylamine cooled to 5° C. and the mixture was stirred for 16 hours and then vacuum filtered. The residue was chromatographed over silica gel and was eluted with an 8- 2 methylene chloride-acetone mixture to obtain 22 g of m-(n-butoxycarbonylamino)-3-methoxy-crotonanilide melting at 100° C.

Workup

  1. filtrationvacuum filtered
  2. customThe residue was chromatographed over silica gel
  3. washwas eluted with an 8- 2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-54f8e2c5081e47e6a24c97246fbadfd2
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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