Formic Acid → N-(5-Chloro-2-phenoxy-phenyl)-formamide

HRID 449130

Reaction equation

HRID 449130 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:16](O)=[O:17].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([NH:1][CH:16]=[O:17])[CH:7]=1

Participants

7

Reactant 5

HCID 284Formic AcidHCID 667385-Chloro-2-phenoxyanilineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 12290068N-(5-Chloro-2-phenoxy-phenyl)-formamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-amino-5-chloro-2-phenoxybenzene (1.00 g, 4.55 mmol), formic acid (0.34 mL, 9.10 mmol), TBTU (1.46 g, 4.55 mmol), DIEA (2.38 mL, 13.6 mmol) and DCM (20 mL) was stirred at rt for 2 h. The solution was transferred to a separatory funnel, 20 mL of sat. aq. NaHCO3 solution was added and the mixture was extracted DCM. The organics were combined and dried (Na2SO4). Solvent was removed under reduced pressure to give a crude residue which was purified via flash chromatography, eluting with 5% EtOAc in hexanes.

Workup

  1. customThe solution was transferred to a separatory funnel
  2. extractionthe mixture was extracted DCM
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e8058ec2bec9481493262bcce1b83675
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Linked notes

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