tert-Butoxy bis(dimethylamino)methane → HCID 53920947, compound

HRID 1733970Notes

Reaction equation

HRID 1733970 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[C:8]2[S:14][CH:15]=[CH:16][C:7]1=2)=[O:5].C(O[CH:29](N(C)C)[N:30]([CH3:32])[CH3:31])(C)(C)C>C(Cl)Cl>[CH3:29][N:30]([CH:32]=[C:10]1[CH2:11][CH2:12][N:6]([C:4](=[O:5])[C:3]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:2]=2[Cl:1])[C:7]2[CH:16]=[CH:15][S:14][C:8]=2[C:9]1=[O:13])[CH3:31]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 19699079HCID 19699079, compound

Product 1

HCID 53920947HCID 53920947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.0 g of 4,5,6,7-tetrahydro-4-(2-chloro-4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one and 20 ml of tert-butoxy-bis(dimethylamino)methane is heated on a steam bath 2 hours followed by the addition of 10 ml of methylene chloride. The reaction mixture is refluxed for 1 hour. The reaction mixture is evaporated in vacuo to a residue which is diluted with 100 ml of methylene chloride and filtered through a pad of hydrous magnesium silicate. The filtrate is filtered through a short column of silica gel to give 2.45 g of the desired product as a yellow foam.

Workup

  1. temperatureis heated on a steam bath 2 hours
  2. temperatureThe reaction mixture is refluxed for 1 hour
  3. customThe reaction mixture is evaporated in vacuo to a residue which
  4. additionis diluted with 100 ml of methylene chloride
  5. filtrationfiltered through a pad of hydrous magnesium silicate
  6. filtrationThe filtrate is filtered through a short column of silica gel

Sources & evidence

ORD record
ord-861c80a8a61c45b8adb375573a97965d
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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