Hydrochloric Acid → HCID 11243733, compound

HRID 1178202Notes

Reaction equation

HRID 1178202 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[C:19]([CH:21]=O)[N:20]=3)[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C1COCC1.II.Cl.O.[NH3:32]>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[C:19]([C:21]#[N:32])[N:20]=3)[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028TetrahydrofuranHCID 12896473Azane;hydrateHCID 86595724HCID 86595724, compound

Product 1

HCID 11243733HCID 11243733, compound

Procedure

To a stirring solution of the crude aldehyde 9a (35 mg, 0.11 mmol) in 1 mL of ammonia water 28% solution and 0.1 mL of THF at rt was added iodine (32 mg, 0.12 mmol). The dark solution became colorless after 1 h of stirring. The reaction mixture was neutralized with 0.5 mL of a 1M aqueous solution of HCl and extracted with ether. Concentrated in vacuo and passed through a short pad of silica gel (30% ethyl acetate/70% hexanes) to give 20 mg (59%) of pure 10.

Workup

  1. extractionextracted with ether
  2. concentrationConcentrated in vacuo
  3. customto give 20 mg (59%) of pure 10

Sources & evidence

ORD record
ord-6710f12b1d22473e94999cf709534aa9
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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