Isoamyl Nitrite → HCID 86714683, compound

HRID 2172665Notes

Reaction equation

HRID 2172665 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][C@H:14]2[C@@H:18]3[O:19][C:20]([CH3:23])([CH3:22])[O:21][C@@H:17]3[C@@H:16]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:15]2)=[N:4][C:5]([S:9][CH2:10][CH2:11][CH3:12])=[N:6][C:7]=1[Cl:8].C(O[N:35]=O)CC(C)C>C(#N)C>[Cl:8][C:7]1[C:2]2[N:1]=[N:35][N:13]([C@H:14]3[C@@H:18]4[O:19][C:20]([CH3:22])([CH3:23])[O:21][C@@H:17]4[C@@H:16]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:15]3)[C:3]=2[N:4]=[C:5]([S:9][CH2:10][CH2:11][CH3:12])[N:6]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 86714684HCID 86714684, compound

Product 1

HCID 86714683HCID 86714683, compoundYield 92.68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 8a (10 g) in acetonitrile (100 mL) was added isoamylnitrite (4.0 g) at 10-30° C. The reaction mixture was stirred at 50-70° C. for 3-5 h. The reaction was monitored by TLC. After completion, the reaction was quenched with 10% aqueous NaHSO3 (10 ml) and concentrated under reduced pressure. The obtained residue was extracted with ethyl acetate (10 vol). The extract was washed with water and then concentrated at reduced pressure to provide the product (9.5 g, 92.68%).

Workup

  1. customAfter completion, the reaction was quenched with 10% aqueous NaHSO3 (10 ml)
  2. concentrationconcentrated under reduced pressure
  3. extractionThe obtained residue was extracted with ethyl acetate (10 vol)
  4. washThe extract was washed with water
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-090bda29c3d547668a7725cdec8e5af1
Source dataset
uspto-grants-2015_06
Patent number
US09056838B2

Reaction notes

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