N,N-Dimethylaniline → HCID 22716514, compound

HRID 1582937Notes

Reaction equation

HRID 1582937 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.CN(C)C1C=CC=CC=1.Cl[C:23]([N:25]=[C:26]=[O:27])=[O:24]>ClCCl>[C:7]1([CH:5]2[N:6]3[C:23](=[O:24])[NH:25][C:26](=[O:27])[CH:1]=[C:2]3[O:3][CH2:4]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 119708Isocyanatocarbonyl chlorideHCID 15619835HCID 15619835, compound

Product 1

HCID 22716514HCID 22716514, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methyl-4-phenyl-4,5-dihydrooxazole (5.70 g, 35.4 mmol) and N,N-dimethylaniline (4.68 g, 6.83 mmol) in dichloromethane (25 mL) at 0° C. was added dropwise chlorocarbonyl isocyanate (3.80 g, 35.4 mmol). The mixture was allowed to warm to room temperature and was stirred for 14 h, during which time a thick white precipitate formed. The suspension was filtered, and the solid was triturated with diethyl ether (3×10 mL) to give a white powder (8.07 g, 99%). 1H NMR (TMS/CDCl3, 300 MHz): 7.44-7.24 (m, 5H); 5.57 (dd, J=3.3, 8.1 Hz, 1H), 5.12 (s, 1H); 5.00 (dd, J=8.1, 8.7 Hz, 1H); 4.54 (dd, J=3.3, 8.7 Hz, 1H); 3.04 (s, 1H). MS=231.0 ((M+H)+).

Workup

  1. customformed
  2. filtrationThe suspension was filtered
  3. customthe solid was triturated with diethyl ether (3×10 mL)

Sources & evidence

ORD record
ord-e7fec08009c84f5cb6d5033f564b8fa0
Source dataset
uspto-grants-2004_05
Patent number
US06740656B2

Reaction notes

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