Triethylamine → HCID 118115071, compound

HRID 1050625Notes

Reaction equation

HRID 1050625 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH:5][CH3:6].CCN(CC)CC.ClC(Cl)(OC(=O)[O:26][C:27]([Cl:30])(Cl)Cl)Cl.CCOC(C)=O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]([CH3:6])[C:27]([Cl:30])=[O:26])[CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 21354505HCID 21354505, compound

Product 1

HCID 118115071HCID 118115071, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

3-Chloro-N-methyl-5-(trifluoromethyl)aniline (519, 1.24 g, 5.9 mmol) was dissolved in 15 mL dry toluene. To it was added Et3N (1.1 mL, 7.9 mmol), and the mixture was stirred in ice bath. To it was drop-wise added a pre-made solution of triphosgene (2.46 g, 8.3 mmol) in 7.5 mL dry toluene. The mixture was then stirred in ice bath for 3 hours. EtOAc (120 mL) and water (50 mL) were then poured into the mixture, and the organic phase was separated. It was washed with saturated NaHCO3 (aq) solution, dried, concentrated in vacuo to afford crude 3-chloro-5-(trifluoromethyl)phenyl(methyl)carbamic chloride (520) as an oil.

Workup

  1. stirringThe mixture was then stirred in ice bath for 3 hours
  2. customthe organic phase was separated
  3. washIt was washed with saturated NaHCO3 (aq) solution
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f58c381f5da41158115dc95cb64b164
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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