Toluene → Methyl 5-iodo-2-isothiocyanatobenzoate

HRID 1276615Notes

Reaction equation

HRID 1276615 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].[C:26](Cl)(Cl)=[S:27]>O.C(O)CC>[I:13][C:10]1[CH:11]=[CH:12][C:3]([N:2]=[C:26]=[S:27])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 22116523Methyl 2-amino-5-iodobenzoate hydrochloride

Product 1

HCID 14663020Methyl 5-iodo-2-isothiocyanatobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 10311-PropanolSolvent

Procedure

To 20 g (0.064 mol) of methyl 2-amino-5-iodobenzoate hydrochloride was added 720 mL of toluene, 180 mL of water, 49 g (0.593 mol) of sodium bicarbonate, and 13.2 mL (0.181 mol) of thiophosgene. The biphasic mixture was stirred at room temperature overnight, diluted with 400 mL of water, and the phases were separated. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to deliver 21.43 g of the title compound, which was used without further purification, 1H NMR (300 MHz, CDCl3): δ3.97 (s,3H); 7.02 (d,1H); 7.81 (dd,1H); 8.30 (d,1H). An analytical sample was prepared by treating 0.30 g of the crude material with 5 mL of n-propanol, followed by the dropwise addition of water. The ensuing precipitate was filtered to deliver 259 mgs of purified methyl 5-iodo-2-isothiocyanatobenzoate, m.p. 60-62° C.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customwas used without further purification, 1H NMR (300 MHz, CDCl3): δ3.97 (s,3H); 7.02 (d,1H); 7.81 (dd,1H); 8.30 (d,1H)
  6. customAn analytical sample was prepared
  7. filtrationThe ensuing precipitate was filtered

Sources & evidence

ORD record
ord-ed5ed0289d734d9598da4ff64b0cce7a
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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