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

HRID 2294082
Notes
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Reaction equation

HRID 2294082 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 18366337
Propan-2-one--water (1/1)
Solvent
HCID 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-d088bffdfe7141dd9bffd6d7b13dd724
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05688792

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes