Hydrochloric Acid → HCID 10943393, compound

HRID 385182Notes

Reaction equation

HRID 385182 reaction equation
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11].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]=[CH:7][C:8]([OH:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])=[C:1]=[S:3]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 40755-Aminosalicylic AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24437Sodium Sulfite

Product 1

HCID 10943393HCID 10943393, compoundYield 100%

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 5-amino-2-hydroxybenzoic acid (0.23 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 17 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 5 minutes at 0° C., followed by stirring at 0° C. for further 2.5 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 5-isothiocyanato-2-hydroxybenzoic acid as a gray solid (0.29 g, yield: 100%, HPLC purity: 97%, HPLC retention time: 4.3 min). LC-MS ES-194 (retention time: 4.4 min, condition 1).

Workup

  1. customThe obtained reaction mixture
  2. stirringby stirring at 0° C. for further 2.5 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-a2c295b4e13c46a1b7768c749f529b76
Source dataset
uspto-grants-2013_02
Patent number
US08367857B2

Reaction notes

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