Isoamyl Nitrite → HCID 68380313, compound

HRID 2178662Notes

Reaction equation

HRID 2178662 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9](N)[S:10][C:6]=2[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.N(OCCC(C)C)=O>O1CCOCC1>[F:1][C:2]1[C:7]2[N:8]=[CH:9][S:10][C:6]=2[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 717431044-Fluoro-7-methoxy-1,3-benzothiazol-2-amine

Product 1

HCID 68380313HCID 68380313, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-fluoro-7-methoxy-1,3-benzothiazol-2-amine (C12) (15.40 g, 77.69 mmol) in 1,4-dioxane (700 mL) was added isoamyl nitrite (15.0 mL, 111.6 mmol). The reaction mixture was stirred at 85° C. for 18 hours and then cooled to room temperature. The solvent was removed in vacuo, and purification was carried out with silica gel chromatography (Eluant: 1:1 dichloromethane/hexanes) to afford the title compound as a yellow solid. Yield: 12.0 g, 65.5 mmol, 84%. 1H NMR (300 MHz, CDCl3) δ 3.98 (s, 3H), 6.77 (m, 1H), 7.16 (m, 1H), 8.98 (s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed in vacuo, and purification

Sources & evidence

ORD record
ord-6c381896e2504f17ad0bbbdf6ec2e553
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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