Methanesulfonic Acid → 1-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

HRID 1626969Notes

Reaction equation

HRID 1626969 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([NH2:14])=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1.CS(O)(=O)=O.[N:20](OCCC(C)C)=O>C(O)C.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[C:6]3[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=3[N:14]=[N:20]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8053Isoamyl NitriteHCID 70197765HCID 70197765, compound

Product 1

HCID 686570341-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N1-(Cyclopropylmethyl)-4-methoxybenzene-1,2-diamine (10.8 g, 56.2 mmol) was dissolved in ethanol (80 mL) and treated with methanesulfonic acid (3.65 ml, 56.2 mmol) followed by isoamyl nitrite (7.56 ml, 56.2 mmol). The mixture was stirred for 15 minutes, diluted with ethyl acetate (1500 mL) and washed with saturated bicarbonate solution (500 mL×2). The organic extracts were concentrated in vacuo, providing a dark solid. The residue was purified by silica gel gradient chromatography (5-50% ethyl acetate in heptanes), providing the titled compound as a tan solid.

Workup

  1. washwashed with saturated bicarbonate solution (500 mL×2)
  2. concentrationThe organic extracts were concentrated in vacuo
  3. customproviding a dark solid
  4. customThe residue was purified by silica gel gradient chromatography (5-50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-f5f2641a80ff466ea76c70a44defad32
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

Loading…