2-Iodobenzoic acid → HCID 9801040, compound

HRID 1419394Notes

Reaction equation

HRID 1419394 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.C([N:30]([CH2:33]C)CC)C.[N+:35]([C:38]1[CH:39]=[CH:40][C:41]([NH2:45])=[C:42]([OH:44])[CH:43]=1)([O-:37])=[O:36]>CN(C=O)C>[OH:44][C:42]1[CH:43]=[C:38]([N+:35]([O-:37])=[O:36])[CH:39]=[CH:40][C:41]=1[NH:45][C:33]([NH:30][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[I:1])=[O:18]

Participants

6

Reactant 4

HCID 69412-Iodobenzoic acidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 9801040HCID 9801040, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The urea was synthesized by the treatment of 2-iodo benzoic acid(5 g, 20 mmol) with diphenyl phosphoryl azide(1 equiv.) and triethyl amine (1 equiv.) in DMF at 80° C. after gas evolution ceased the 5-nitro 2-amino phenol (3 g, 1 equiv.) was added. The reaction was heated overnight at 80° C. The reaction mixture was purified by filtering through a plug of silica with methylene chloride. The desired product was then precipitated out with hexane. Filtering afforded the desired compound(1.08 g, 13%). EI-MS m/z 398(M-H)-

Workup

  1. additionwas added
  2. customThe reaction mixture was purified
  3. filtrationby filtering through a plug of silica with methylene chloride
  4. customThe desired product was then precipitated out with hexane
  5. filtrationFiltering

Sources & evidence

ORD record
ord-0cc2255545b842fb940315e9fc7a302f
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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