Methyl chloroformate → HCID 49764241, compound

HRID 1160096Notes

Reaction equation

HRID 1160096 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C:18]2=[O:23])=[CH:13][CH:12]=1.Cl[C:25]([O:27][CH3:28])=[O:26]>C(Cl)Cl>[O:23]=[C:18]1[CH2:19][O:20][CH2:21][CH2:22][N:17]1[C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:25](=[O:26])[O:27][CH3:28])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 111948544-(4-Aminophenyl)morpholin-3-one

Product 1

HCID 49764241HCID 49764241, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (27.2 mL, 156.08 mmol) was added over 3 min to a stirred suspension of 4-(4-aminophenyl)-3-morpholinone (2, 25 g, 130.07 mmol) in CH2Cl2 (750 mL). The reaction mixture was stirred at room temperature for 15 min and methyl chloroformate (11.6 mL, 149.58 mmol) was added drop-wise over 10 min. The resulting thick suspension was stirred for another 1 h and filtered through a Buchner funnel. The solid was washed with CH2Cl2 (2×75 mL) and dried under vacuum to obtain methyl N-[4-(3-oxo-4-morpholinyl)phenyl]carbamate (5b, 30.92 g, 95%) as a crystalline solid.

Workup

  1. stirringThe resulting thick suspension was stirred for another 1 h
  2. filtrationfiltered through a Buchner funnel
  3. washThe solid was washed with CH2Cl2 (2×75 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f106aecb396d48e98e7ac12d16e617c1
Source dataset
uspto-grants-2010_10
Patent number
US07816355B1

Reaction notes

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