tert-Butoxy bis(dimethylamino)methane → 5-Dimethylaminomethylene-6,7-dihydro-5H-benzo[1,2,5]oxadiazol-4-one

HRID 643758Notes

Reaction equation

HRID 643758 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]=12.CC(O[CH:16](N(C)C)[N:17]([CH3:19])[CH3:18])(C)C>C1COCC1>[CH3:16][N:17]([CH:19]=[C:8]1[C:9](=[O:10])[C:4]2=[N:3][O:2][N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:18]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 5430526,7-Dihydro-2,1,3-benzoxadiazol-4(5H)-one

Product 1

HCID 674055215-Dimethylaminomethylene-6,7-dihydro-5H-benzo[1,2,5]oxadiazol-4-oneYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution of 4,5,6,7-tetrahydro-2,1,3-benzoxadiazole-4-one 1 g (0.00725 mol) and Bredereck's reagent 1.89 g (0.0109 mol) was stirred at room temperature for 2 days. The crystalline precipitate was filtered, washed with THF and dried, 0.8 g desired product was obtained, the yield is 57%.

Workup

  1. filtrationThe crystalline precipitate was filtered
  2. washwashed with THF
  3. customdried

Sources & evidence

ORD record
ord-dbf66afe45544f3f84f61f2e02ee941a
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Reaction notes

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