Triethylamine → HCID 83799798, compound

HRID 924284Notes

Reaction equation

HRID 924284 reaction equation
[CH2:1]([C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].C(N(CC)CC)C.[C:19](Cl)(Cl)=[S:20]>ClCCl>[CH2:1]([C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[N:5]=[C:19]=[S:20])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 22065597114747-31-8

Product 1

HCID 83799798HCID 83799798, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 2-ethyl-4-methoxyaniline (4.5 g, 30 mmol) and triethylamine (6.0 g, 60 mmol) in dichloromethane (31 mL) was added thiophosgene (3.4 g, 30 mmol) was added drop wise at 0° C. over the period of 1 hour. After completion, the reaction mixture was poured into ice-water (100 mL) and extracted with ethyl acetate (3×200 mL) and washed with ice water (2×100 mL), followed by brine (2×50 mL). The organic phase was dried over sodium sulfate, filtered, and evaporated under reduced pressure. Purification by flash column chromatography using 0-10% ethyl acetate/hexanes as eluent provided 2-ethyl-1-isothiocyanato-4-methoxybenzene as yellow oil (4.9 g, 25 mmol), which was taken onto the next step immediately.

Workup

  1. additionwas added drop wise at 0° C. over the period of 1 hour
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washwashed with ice water (2×100 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-d348630209744cc5b012eb3570510506
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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