Ethyl Acetate → Phenylmethyl N-[3,5-difluoro-4-(4-morpholinyl)phenyl]carbamate

HRID 1417945Notes

Reaction equation

HRID 1417945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:15])[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:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(OCC)(=O)C>CC(C)=O.O.[Cl-].[Na+].O>[C:22]([NH:5][C:4]1[CH:3]=[C:2]([F:1])[C:8]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:7]([F:15])[CH:6]=1)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 218781683,5-Difluoro-4-(morpholin-4-yl)aniline

Product 1

HCID 129071887Phenylmethyl N-[3,5-difluoro-4-(4-morpholinyl)phenyl]carbamate

Reagents, catalysts & solvents 2

HCID 18366337Propan-2-one--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.518 g of 3,5-difluoro-4-morpholinyl-aniline and 0.432 g of sodium bicarbonate in 20 mL of acetone:water (2:1 v/v) at 0° C. was added 0.36 mL of benzyl chloroformate over 2 minutes. After 5.5 hours, the mixture was allowed to warm to ambient temperature and after an additional 2.6 hours, the mixture was added to 25 mL of ethyl acetate and 20 mL of brine. The aqueous layer was extracted with 3×25 ml of ethyl acetate and the combined organic layers were dried (MgSO4), and concentrated in vacuo to give a solid, mp=131°-133° C.

Workup

  1. extractionThe aqueous layer was extracted with 3×25 ml of ethyl acetate
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a solid, mp=131°-133° C.

Sources & evidence

ORD record
ord-3896efa7c5c440c6a25664711a0bf4dd
Source dataset
uspto-grants-1999_03
Patent number
US05880118

Reaction notes

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