Formamide → HCID 58424802, compound

HRID 1408800Notes

Reaction equation

HRID 1408800 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=O.[C-]#[N:20].[K+].[CH:22]([NH2:24])=[O:23].CCO[C:28](C)=[O:29]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]12[C:22](=[O:23])[NH:24][C:28](=[O:29])[NH:20]1

Participants

5

Reactant 4

HCID 713FormamideHCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 58424213HCID 58424213, compound

Product 1

HCID 58424802HCID 58424802, compound

Conditions

Temperature
65 °C

Procedure

To a 10 mL CEM microwave test tube charged with 6-bromo-2-phenylthiochroman-4-one (344 mg, 1.08 mmol), KCN (150 mg, 2.2 mmol), and (NH4)2CO3 (800 mg, 7.7 mmol) is added formamide (6.5 mL). The resulting mixture is heated in a CEM microwave reactor at 60° C. for 1.5 hrs, 65° C. for 1.5 hrs, then 70° C. for 2 hrs. The resulting mixture is diluted with EtOAc (20 mL) and washed with H2O (3×10 mL). The organic layer is dried over Na2SO4, and solvent is removed in vacuo to give a crude product, which is purified by flash chromatography column (0 to 60% EtOAc/hexane) to give the 6′-bromo-2′-phenylspiro[imidazolidine-4,4′-thiochroman]-2,5-dione (237 mg). MS ESI+ve m/z 389 (M+H)+.

Workup

  1. washwashed with H2O (3×10 mL)
  2. dry with materialThe organic layer is dried over Na2SO4, and solvent
  3. customis removed in vacuo
  4. customto give a crude product, which
  5. customis purified by flash chromatography column (0 to 60% EtOAc/hexane)

Sources & evidence

ORD record
ord-7388da79a04e485e998b7d6301747f92
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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