Hydrochloric Acid → HCID 15396781, compound

HRID 385180Notes

Reaction equation

HRID 385180 reaction equation
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9].C(N(CC)CC)C.II.Cl.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1.O>[N:4]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])=[C:1]=[S:3]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 755683-Amino-4-methylbenzoic acid

Product 1

HCID 15396781HCID 15396781, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 3-amino-4-methylbenzoic acid (0.23 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 26 hours. The obtained reaction mixture was dropwise added to a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) over a period of two minutes at 0° C., followed by stirring at 0° C. for further two hours. Thereafter, 1M hydrochloric acid (1.5 mL) and sodium sulfite (38 mg, 0.30 mmol) were added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and concentrated under reduced pressure to dryness. To the residue, ethyl acetate (6 mL) and water (1 mL) were added, and the organic layer was concentrated under reduced pressure to dryness to obtain 3-isothiocyanato-4-methylbenzoic acid as a ocher solid (0.26 g, yield: 91%, HPLC purity: 95%, HPLC retention time: 3.9 min). LC-MS ES-192 (retention time: 4.3 min, condition 1).

Workup

  1. customThe obtained reaction mixture
  2. stirringby stirring at 0° C. for further two hours
  3. additionmixed
  4. customthe organic layer was separated
  5. concentrationconcentrated under reduced pressure to dryness
  6. additionTo the residue, ethyl acetate (6 mL) and water (1 mL) were added
  7. concentrationthe organic layer was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-69117a708de94f8fb6331e8ddc3d8bfe
Source dataset
uspto-grants-2013_02
Patent number
US08367857B2

Reaction notes

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