tert-Butoxy bis(dimethylamino)methane → HCID 54555844, compound

HRID 1457648Notes

Reaction equation

HRID 1457648 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15](=[O:22])[CH2:14][CH2:13][CH2:12]1)(=[O:10])=[O:9].C(O[CH:28](N(C)C)[N:29]([CH3:31])[CH3:30])(C)(C)C>ClCCl>[CH3:28][N:29]([CH:31]=[C:14]1[C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:11]([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])(=[O:10])=[O:9])[CH2:12][CH2:13]1)[CH3:30]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 22099592HCID 22099592, compound

Product 1

HCID 54555844HCID 54555844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.89 g of 1,2,3,4-tetrahydro-1-[(2-methylphenyl)sulfonyl]-5H-1-benzazepin-5-one and 2.47 ml of tert-butoxy-bis(dimethylamino)methane (Bredericks reagent) in 10 ml of dichloromethane is heated under argon on a steam bath for 16 hours. The mixture is concentrated to dryness under vacuum and the residue dissolved in CH2Cl2. The solution is filtered through a thin pad of hydrous magnesium silicate and the pad washed with 5% ethyl acetate in CH2Cl2. The filtrate is concentrated to dryness and the residue (1.96 g) crystallized from CH2Cl2 -hexane to give 0.85 g of crystals, m.p. 180°-185° C. A second crop of crystals (0.85 g) is recovered from the mother liquors and an additional 0.30 g is recovered from washing the pad of hydrous magnesium silicate with ethyl acetate.

Workup

  1. temperatureis heated under argon on a steam bath for 16 hours
  2. concentrationThe mixture is concentrated to dryness under vacuum
  3. dissolutionthe residue dissolved in CH2Cl2
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with 5% ethyl acetate in CH2Cl2
  6. concentrationThe filtrate is concentrated to dryness
  7. customthe residue (1.96 g) crystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-b4e9929317f64620ad6bc16c72c548cb
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

Loading…