Hexyl isocyanate → 1-Hexyl-3-(5-nitrobenzo[d]isothiazol-3-yl)urea

HRID 1409991Notes

Reaction equation

HRID 1409991 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([NH2:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].[N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:15]=[O:16]>C1COCC1>[CH2:17]([NH:14][C:15]([NH:12][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[S:11][N:10]=1)=[O:16])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 75659Hexyl isocyanate2×HCID 1586383-Amino-5-nitrobenzisothiazole

Product 1

HCID 120014201-Hexyl-3-(5-nitrobenzo[d]isothiazol-3-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

100 mg (0.513 mmol) of 5-nitrobenzo[d]isothiazol-3-ylamine were suspended in 5 ml of THF. Addition of 78.1 mg (0.61 mmol) of 1-isocyanatohexane was followed by stirring at RT for 2 h and at 70° C. for 2 h. Then a further 0.3 mmol of 1-isocyanatohexane was added, and stirring was continued at 70° 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: 18 mg (11%), M+H+: 323.15.

Workup

  1. stirringstirring
  2. waitwas continued at 70° C. for 6 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic phase was concentrated
  7. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-1f78192f084d42d38cfcc2d2ac11c1be
Source dataset
uspto-grants-2014_12
Patent number
US08921404B2

Reaction notes

Loading…