Toluene → 5-Methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester

HRID 895335Notes

Reaction equation

HRID 895335 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH2:11].C(N(CC)CC)C.[C:20](Cl)(Cl)=[O:21].C1(C)C=CC=CC=1.[C:31]1([SH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[N-]=C=O>C1COCC1>[CH3:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][C:20]([S:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21])=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:12]

Participants

8

Reactant 6

HCID 1140TolueneHCID 6371PhosgeneHCID 7969ThiophenolHCID 8471TriethylamineHCID 105034IsocyanateHCID 1201104Methyl 2-Amino-5-methylbenzoate

Product 1

HCID 865895625-Methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-methylbenzoic acid methyl ester (122 mg, 0.79 mmol) and triethylamine (0.28 ml, 1.96 mmol) were dissolved in THF (10 ml). A 20% solution of phosgene in toluene (0.74 ml, 1.6 mmol) was added, causing immediate formation of a white precipitate. After 1 h, excess phosgene was purged with a stream of nitrogen, the vented gas being passed through a base scrubber. Thiophenol (81 μl, 0.79 mmol) was added to this crude isocyanate solution, which was then stirred for 1 h. The mixture was filtered to remove triethylamine hydrochloride, the solid being washed with ether. After concentration of the filtrate, the residue was purified by flash chromatography (5% to 10% EtOAc/petrol) to give 5-methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester: m/z (ES+) 300 (M−H).

Workup

  1. customexcess phosgene was purged with a stream of nitrogen
  2. filtrationThe mixture was filtered
  3. customto remove triethylamine hydrochloride
  4. washthe solid being washed with ether
  5. customAfter concentration of the filtrate, the residue was purified by flash chromatography (5% to 10% EtOAc/petrol)

Sources & evidence

ORD record
ord-495e76e74eb444b7a49d4aad3c7e7a50
Source dataset
uspto-grants-2005_07
Patent number
US06916808B2

Reaction notes

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