Water → HCID 66760184, compound

HRID 389575Notes

Reaction equation

HRID 389575 reaction equation
[I:1][C:2]1[C:10]2[S:9][C:8]([CH2:11][O:12][CH3:13])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1N.N(OC(C)(C)C)=O.O>C1COCC1>[I:1][C:2]1[C:10]2[S:9][C:8]([CH2:11][O:12][CH3:13])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 66760862HCID 66760862, compound

Product 1

HCID 66760184HCID 66760184, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a cooled (0° C.) solution of 7-iodo-2-methoxymethyl-benzothiazol-6-ylamine (1.8 g, 5.62 mmol) in THF under nitrogen was added tert-butyl nitrite (3.3 mL, 28.1 mmol) dropwise. The reaction mixture stirred 3 h at 50° C. Water was added and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by column chromatography afforded 1.0 g (60%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.90 (d, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.19-7.21 (m, 1H), 4.8 (s, 2H), 3.58 (s, 3H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic fractions were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-0b86e69217614875a73576df6785d4e0
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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