Triethylamine → O-3-Isopropyl-5-methyl-phenyl N,N-bis-fluoromethyl-carbamate

HRID 1448014Notes

Reaction equation

HRID 1448014 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1)([CH3:3])[CH3:2].[F:12][CH2:13][N:14]([CH2:18][F:19])[C:15](F)=[O:16].C(N(CC)CC)C>C(Cl)Cl>[F:12][CH2:13][N:14]([CH2:18][F:19])[C:15](=[O:16])[O:11][C:6]1[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 728555-Isopropyl-m-cresolHCID 54418525N,N-bis-fluoromethyl-carbamic acid fluoride

Product 1

HCID 70603906O-3-Isopropyl-5-methyl-phenyl N,N-bis-fluoromethyl-carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
40 °C

Procedure

16 parts of 80 percent strength by weight 3-isopropyl-5-methyl-phenol in 30 parts of methylene chloride are added to 12.7 parts of N,N-bis-fluoromethyl-carbamic acid fluoride (from Example 2) in 50 parts of methylene chloride. 10.1 parts of triethylamine in 20 parts of methylene chloride are then added. The reaction mixture is stirred for one hour at 40° C. and when it has cooled it is extracted by shaking with 10 percent strength by weight sodium hydroxide solution and water, dried and distilled to dryness under reduced pressure. 24.1 parts (95% of theory) of O-3-isopropyl-5-methyl-phenyl N,N-bis-fluoromethyl-carbamate of boiling point 120° C./0.05 mm Hg are obtained.

Workup

  1. temperaturewhen it has cooled it
  2. extractionis extracted
  3. stirringby shaking with 10 percent strength by weight sodium hydroxide solution and water
  4. customdried
  5. distillationdistilled to dryness under reduced pressure

Sources & evidence

ORD record
ord-4eb8427198f140188a6be90a394d7d84
Source dataset
uspto-grants-1979_12
Patent number
US04179465

Reaction notes

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