tert-Butoxy bis(dimethylamino)methane → HCID 1473179, compound

HRID 2047245Notes

Reaction equation

HRID 2047245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]#[N:15])=[C:12]([CH3:16])[O:11][N:10]=1.C(O[CH:22](N(C)C)[N:23]([CH3:25])[CH3:24])(C)(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]#[N:15])=[C:12](/[CH:16]=[CH:22]/[N:23]([CH3:25])[CH3:24])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 27365803-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonitrile

Product 1

HCID 1473179HCID 1473179, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.5 g (6.3389 mmol) 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonitrile in 100 mL dry toluene, were added 2.10 g (12.6779 mmol) tert-Butoxy-bis(dimethylamino)methane. The reaction mixture was heated under reflux for 12 h. The mixture was concentrated in vacuo and was dried in the high vacuum. Petroleum ether was added to the crystallized residue. The product was collected by filtration and 1.791 g (yield of theory: 95.9%) of clean product were obtained. Result of LC/MS MH+: 292.0; 1H NMR (DMSO-d6; CCl4): 2.93 (3H, s, N—CH3), 3.17 (3H, s, N—CH3), 5.15-5.20 (1H, d, C2H2), 7.74-7.78 (1H, d C2H2), 7.45-7.52 (1H, dd, CH-arom.), 7.57-7.59 (1H, d, CH-arom.), 7.65-7.71 (1H, d, CH-arom.)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customwas dried in the high vacuum
  5. additionPetroleum ether was added to the crystallized residue
  6. filtrationThe product was collected by filtration and 1.791 g (yield of theory: 95.9%) of clean product
  7. customwere obtained
  8. customResult of LC/MS MH+

Sources & evidence

ORD record
ord-513f6836cb6b4accb88b69f7b2794d59
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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