tert-Butoxy bis(dimethylamino)methane → HCID 67272642, compound

HRID 601444Notes

Reaction equation

HRID 601444 reaction equation
[C:1]([C:4]1[S:8][C:7](=[O:9])[NH:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].C(O[CH:16](N(C)C)[N:17]([CH3:19])[CH3:18])(C)(C)C>CCOC(C)=O>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:2][C:1]([C:4]1[S:8][C:7](=[O:9])[NH:6][C:5]=1[CH3:10])=[O:3]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 21793266HCID 21793266, compound

Product 1

HCID 67272642HCID 67272642, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5-Acetyl-4-methyl-3H-thiazol-2-one (0.5 g, 3.18 mmol) and tert-butoxy-bis(dimethylamino)methane (Bredereck's reagent; 2.226 mL, 0.477 mmol) were combined and heated at 80° C. for 4 h. Removal of the excess solvent under reduced pressure gave a dark residue. Treatment of this residue with EtOAc afforded the title compound as a solid product, which was collected by filtration (0.074 g, 11%). Anal. RP-HPLC: tR 10.5 min (0-60% MeCN over 20 min). 1H-NMR (DMSO-d6): δ2.33 (3H, s, CH3), 2.70 (3H, s, NCH3), 3.09 (3H, s, NCH3), 5.07 (1H, d, CH, J=12.0), 7.55 (1H, d, J=12.0, CH), 11.23 (1H, s, NH). MS (ESI+) m/z 213.44 (M+H)+.

Workup

  1. customRemoval of the excess solvent under reduced pressure
  2. customgave a dark residue

Sources & evidence

ORD record
ord-f1f3391f1a474c1a8f8a086cdced0247
Source dataset
uspto-grants-2011_03
Patent number
US07902361B2

Reaction notes

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