Iodine chloride → HCID 66760862, compound

HRID 389574Notes

Reaction equation

HRID 389574 reaction equation
[I:1]Cl.[CH3:3][O:4][CH2:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:9]=2[N:10]=1.C(=O)(O)[O-].[Na+]>O.Cl>[I:1][C:14]1[C:8]2[S:7][C:6]([CH2:5][O:4][CH3:3])=[N:10][C:9]=2[CH:11]=[CH:12][C:13]=1[NH2:15]

Participants

6

Reactant 3

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 65438164HCID 65438164, compound

Product 1

HCID 66760862HCID 66760862, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of iodine monochloride in water (1.5 mL) and 12 N hydrochloric acid (0.46 mL) was added 2-methoxymethyl-benzothiazol-6-ylamine (0.5 g, 2.57 mmol) in water (3 mL) and 12 N hydrochloric acid (0.23 mL). The reaction mixture stirred at RT for 2 h and was then neutralized with saturated aqueous sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. Purification of the residue by column chromatography (20 to 30% ethyl acetate:hexanes) afforded 800 mg (91%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.74 (d, J=8.7 Hz, 1H), 6.86 (d, J=8.7 Hz, 1H), 4.77 (s, 2H), 4.23 (br. s, 2H), 3.53 (s, 3H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by column chromatography (20 to 30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-76fa1e7ccf6f4e379f6b9fd7a032bcbe
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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