2-Oxopropanethioamide → 6'-Bromo-5-methyl-5'',6''-dihydro-4''H-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4(3H)-thione

HRID 1770964Notes

Reaction equation

HRID 1770964 reaction equation
O=[C:2]([CH3:6])[C:3](=[S:5])[NH2:4].[Br:7][C:8]1[CH:9]=[C:10]2[C:20](=[CH:21][CH:22]=1)[O:19][C:13]1([CH2:18][CH2:17][CH2:16][O:15][CH2:14]1)[CH2:12][C:11]2=[NH:23]>C(#N)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:20](=[CH:21][CH:22]=1)[O:19][C:13]1([CH2:18][CH2:17][CH2:16][O:15][CH2:14]1)[CH2:12][C:11]12[NH:4][C:3](=[S:5])[C:2]([CH3:6])=[N:23]1

Participants

4

Reactant 2

HCID 207652372-Oxopropanethioamide2×HCID 679793356-Bromo-5',6'-dihydro-4'H-spiro[chromene-2,3'-pyran]-4(3H)-imine

Product 1

HCID 866672766'-Bromo-5-methyl-5'',6''-dihydro-4''H-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4(3H)-thione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Oxopropanethioamide (Intermediate 2, 289 mg, 2.80 mmol) and 6-bromo-5′,6′-dihydro-4′H-spiro[chromene-2,3′-pyran]-4(3H)-imine (Example 45 Step 2, 331.4 mg, 1.12 mmol) were dissolved in acetonitrile (3 mL) and heated using MW for 20 min to 120° C. The solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography using a gradient of 0-50% EtOAc in heptane but co-eluted with byproducts. The not completely pure product was used as a mixture in the next step.

Workup

  1. temperatureheated
  2. customThe solvent was evaporated under reduced pressure
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-9d4717accfdb4d71bc598828efb50c50
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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