Isoamyl Nitrite → HCID 18668838, compound

HRID 1058566Notes

Reaction equation

HRID 1058566 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([S:19][CH3:20])[C:3]=1[C:21]#[N:22].N(OCCC(C)C)=O>CN(C=O)C>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=[C:8]([Cl:18])[C:7]=1[N:6]1[CH:2]=[C:3]([C:21]#[N:22])[C:4]([S:19][CH3:20])=[N:5]1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 2741098HCID 2741098, compound

Product 1

HCID 18668838HCID 18668838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methylsulfide 5 (37 mg, 0.1 mmol) in DMF (5 mL) was warmed up to 65° C. and treated dropwise with excess isoamyl nitrite. After a few minutes nitrogen gas bubbled off the reaction mixture. The stirring was continued for 30 min. The reaction was cooled down to room temperature, diluted with ethyl ether (10 mL) and washed with brine (5×15 mL). The organic layer was dried (magnesium sulfate) and the solvents removed at reduced pressure, leaving a dark oil residue The desired product was obtained upon flash chromatography eluting with ethyl acetate-hexanes (5%), to yield 19 mg (54%) of desired product 8. 1H-NMR (δ, CDCl3): 7.95 (1H, s); 7.78 (2H, s); 2.6 (3H; s). MS: M+1=352 (calculated: 352).

Workup

  1. customAfter a few minutes nitrogen gas bubbled off the reaction mixture
  2. additiondiluted with ethyl ether (10 mL)
  3. washwashed with brine (5×15 mL)
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. customthe solvents removed at reduced pressure

Sources & evidence

ORD record
ord-b1767e7380064832927bc2d9064f2875
Source dataset
uspto-grants-2003_02
Patent number
US06518266B1

Reaction notes

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