4-Iodophenol → Methyl-phenyl-carbamic Acid 4-iodo-phenyl Ester

HRID 1180027Notes

Reaction equation

HRID 1180027 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](Cl)=[O:12].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11](=[O:12])[N:10]([CH3:9])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 81531Diisopropylethylamine

Product 1

HCID 69517304Methyl-phenyl-carbamic Acid 4-iodo-phenyl EsterYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-iodophenol (30 mmol) in CH2Cl2 (100 mL) was added N-methyl-N-phenylcarbamoyl chloride (27 mmol) and diisopropylethylamine (60 mmol) at room temperature. The reaction mixture was stirred for 16 hours at rt, added CH2Cl2 (20 mL) and washed with aqueous citric acid (5%), aqueous Na2CO3 and brine. The organic phase was dried (MgSO4) and evaporated to give the crude product which was purified by FC (Quad flash 40 EtOAc-Heptane) to give 6.55 g (69%) of the title compound as light brown crystals.

Workup

  1. washwashed with aqueous citric acid (5%), aqueous Na2CO3 and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give the crude product which
  5. customwas purified by FC (Quad flash 40 EtOAc-Heptane)

Sources & evidence

ORD record
ord-8207f4b894cd49639bb8010419a0d6c1
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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