Triethylamine → HCID 20225716, compound

HRID 1248939Notes

Reaction equation

HRID 1248939 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].C(N(CC)CC)C.[C:20](Cl)(Cl)=[S:21]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11])[CH2:5][N:6]=[C:20]=[S:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 146264691-(3,5-Difluoro-4-methoxyphenyl)methanamine

Product 1

HCID 20225716HCID 20225716, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 3,5-difluoro-4-methoxybenzylamine (8.7 g, 0.05 mole) and triethylamine (15.5 ml, 0.11 mole) in 50 ml of tetrahydrofuran was added dropwise to a solution of thiophosgene (4.2 ml, 0.055 mole) in 50 ml of tetrahydrofuran with cooling to -10° C. over a period of twenty minutes. The mixture was stirred at 25° C. for 2.75 hours and then filtered. The filtrate was treated with charcoal, filtered, and evaporated to an oil. The oil was diluted with hexane:ethyl acetate (90:10) and purified on a flash silica column using hexane:ethyl acetate (90:10) as the eluant to yield 9.2 g (79%) of 3,5-difluoro-4-methoxybenzyl isothiocyanate.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was treated with charcoal
  3. filtrationfiltered
  4. customevaporated to an oil
  5. additionThe oil was diluted with hexane:ethyl acetate (90:10)
  6. custompurified on a flash silica column

Sources & evidence

ORD record
ord-85754a0909664cc7a9a6b9d2034a94e0
Source dataset
uspto-grants-1986_12
Patent number
US04628059

Reaction notes

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