Benzothiazolone → HCID 131729122, compound

HRID 1677649Notes

Reaction equation

HRID 1677649 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].N([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=C=O>N1C=CC=CC=1>[O:10]=[C:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1]1.[CH3:19][CH2:18][CH:17]([C:2]([NH2:3])=[O:10])[CH2:16][CH2:15][CH3:14]

Participants

4

Reactant 2

HCID 13625BenzothiazoloneHCID 75659Hexyl isocyanate2×

Product 1

HCID 131729122HCID 131729122, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

75 mg (0.45 mmol) of 3H-benzothiazol-2-one were dissolved in 10 ml of pyridine. Addition of 76 mg (0.59 mmol) of 1-isocyanatohexane was followed by stirring at 100° C. for 6 h, addition once again of the same amount of isocyanatohexane and stirring at 100° C. for 6 h. The reaction mixture was concentrated, and the residue was dissolved in water and extracted with ethyl acetate. The organic phase was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 38 mg (28%), M+H+: 279.15.

Workup

  1. stirringstirring at 100° C. for 6 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic phase was concentrated
  6. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-9b1d833c617a411dbebe7fb501a5c5b5
Source dataset
uspto-grants-2011_08
Patent number
US08008331B2

Reaction notes

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