Formic Acid → HCID 66640457, compound

HRID 1094482Notes

Reaction equation

HRID 1094482 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=2)=[O:17])=[C:11]([OH:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:33](Br)Br.C(O)=O>CN1C(=O)N(C)CC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]([N:15]2[C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:10][C:11]=3[O:30][CH2:33]2)=[O:17])=[CH:20][C:21]=1[C:26]([F:29])([F:27])[F:28]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 3024DibromomethaneHCID 24758Sodium hydrideHCID 66640094HCID 66640094, compound

Product 1

HCID 66640457HCID 66640457, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To a solution of 1.4 g (3.2 mMol) of 1-(4-benzyloxy-2-hydroxy-phenyl)-3-(4-chloro-3-trifluoromethyl-phenyl)-urea in 420 ml DMEU, 700 mg NaH (55% in oil; 16 mMol) are given. After 15 min, 23 ml of CH2Br2 are added and stirring is continued for 6 h. Then 1 ml of formic acid is added and the resulting mixture is evaporated in HV. The residue is dissolved in EtOAc and water. The separated aq. phase is extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/CH2Cl2 1:1→CH2Cl2) gives the title compound: m.p.: 135-136° C.

Workup

  1. waitis continued for 6 h
  2. customthe resulting mixture is evaporated in HV
  3. dissolutionThe residue is dissolved in EtOAc
  4. extractionThe separated aq. phase is extracted twice with EtOAc
  5. washThe organic layers are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6405acb99d1c49a6937915c91692813a
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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