Butyl nitrite → HCID 18931025, compound

HRID 1598953Notes

Reaction equation

HRID 1598953 reaction equation
N(OCCCC)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:34]=[C:33](N)[CH:32]=[N:31][C:18]=3[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=3)[N:20]=2)=[CH:11][CH:10]=1>C1COCC1>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[CH:34]=[CH:33][CH:32]=[N:31][C:18]=3[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[N:22]=3)[N:20]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 10996Butyl nitrite2×HCID 18931023HCID 18931023, compound

Product 1

HCID 18931025HCID 18931025, compoundYield 128.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of butyl nitrite (0.69 g, 6.66 mol) in THF (15 mL) at reflux under N2 was added a solution of the title compound of Step C (1.30 g, 3.33 mmol) in THF (15 mL) dropwise over 5 min. The dark brown solution was allowed to reflux 2 h. When TLC analysis was inconclusive, additional butyl nitrite (0.35 g, 3.33 mmol) was added. After 1 h, the solution was allowed to cool to room temperature and concentrated in vacuo to give a purple solid (1.6 g). Purification by flash chromatography eluting with 20-30% ethyl acetate/hexanes afforded the title compound of Step D, a compound of the invention, as a brown solid (0.45 g) melting at 67°-72° C. 1H NMR (CDCl3, 300 MHz) δ7.80-8.00 (m,5H), 7.46 (dd, 1H), 7.08-7.16 (m,3H), 6.88 (dd, 1H).

Workup

  1. temperatureto reflux 2 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c603417f56a4d02af51a50689b9a3e7
Source dataset
uspto-grants-1998_04
Patent number
US05739326

Reaction notes

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