N,N-Dimethylaniline → HCID 12991505, compound

HRID 1582936Notes

Reaction equation

HRID 1582936 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[O:6][CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:9]=1.CN(C)C1C=CC=CC=1.Cl[C:30]([N:32]=[C:33]=[O:34])=[O:31]>ClCCl>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]1[C:33](=[O:34])[NH:32][C:30](=[O:31])[N:9]2[CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:7][O:6][C:5]=12

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 119708Isocyanatocarbonyl chlorideHCID 22716523HCID 22716523, compound

Product 1

HCID 12991505HCID 12991505, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2-fluorobenzyl)-4-phenyloxazoline (0.250 g, 0.980 mmol) and N,N-dimethylaniline (0.134 g, 1.09 mmol) in dichloromethane (1.5 mL) at 0° C. was added dropwise chlorocarbonyl isocyanate (0.103 g, 0.980 mmol). The mixture was allowed to warm to room temperature and was stirred for 24 h. The solution was concentrated, dissolved in ethyl acetate (1 mL) and filtered through a short pad of silica gel, eluating with ethyl acetate (150 mL). Concentration gave green-yellow crystals (0.300 g) which were used immediately in the next step due. MS=325.1 ((M+H)+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in ethyl acetate (1 mL)
  3. filtrationfiltered through a short pad of silica gel
  4. concentrationConcentration

Sources & evidence

ORD record
ord-e12cd569d4fe49cab3548777f6d2f127
Source dataset
uspto-grants-2004_05
Patent number
US06740656B2

Reaction notes

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