tert-Butoxy bis(dimethylamino)methane → HCID 58296343, compound

HRID 390054Notes

Reaction equation

HRID 390054 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:12]=[N:13][N:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:15]=2)[N:5]=[C:4]([S:25][CH3:26])[N:3]=1.C(O[CH:32](N(C)C)[N:33]([CH3:35])[CH3:34])(C)(C)C>CN(C=O)C>[CH3:32][N:33]([CH3:35])/[CH:34]=[CH:1]/[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:12]=[N:13][N:14]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:15]=2)[N:5]=[C:4]([S:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 58296320HCID 58296320, compound

Product 1

HCID 58296343HCID 58296343, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of intermediate 29 (4.16 g, 10.8 mmol) in DMF (100 mL) was added tert-butoxy-N,N,N′,N′-tetramethylmethanediamine (BBDM, 5.63 g, 32.3 mmol). The mixture was stirred for 16 h at 100° C. After cooling to room temperature, the mixture was poured into ice-water (800 mL), filtered and the solid was washed with water, petroleum and the mixture solvent (petroleum:ethyl acetate=3:1) successively, dried to obtain 4.2 g of product as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. washthe solid was washed with water, petroleum
  4. dry with materialthe mixture solvent (petroleum:ethyl acetate=3:1) successively, dried

Sources & evidence

ORD record
ord-8842ef03bfac4fe5a286de5aaa97db72
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

Loading…