Benzyl chloroformate → Carbamic acid, N-(3-fluoro-4-(4-morpholinyl)phenyl)-, phenylmethyl ester

HRID 2294084Notes

Reaction equation

HRID 2294084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>CC(C)=O.O>[C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:2]([F:1])[CH:3]=1)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 14853303-Fluoro-4-morpholinoaniline

Product 1

HCID 5306150Carbamic acid, N-(3-fluoro-4-(4-morpholinyl)phenyl)-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 28.91 g of 3-fluoro-4-morpholinyl-aniline and 27.88 g of sodium bicarbonate in 500 mL of acetone and 250 mL of water at 0° C. was added 28.68 g of benzyl chloroformate. After stirring the mixture for 1.5 hours, the mixture was poured onto 1000 cc of ice and water, and the ice allowed to melt. The precipitated solid was collected by filtration and washed with 3×250 ml of water, and then dried in a vacuum oven at 75° C. to give a gray-purple solid. This was recrystallized from acetone-water to give a cream-colored solid, mp=123°-124° C.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with 3×250 ml of water
  3. customdried in a vacuum oven at 75° C.
  4. customto give a gray-purple solid
  5. customThis was recrystallized from acetone-water
  6. customto give a cream-colored solid, mp=123°-124° C.

Sources & evidence

ORD record
ord-b479d57f8bea498193726dc1ec4976d8
Source dataset
uspto-grants-1997_11
Patent number
US05688792

Reaction notes

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