Triethylamine → HCID 22258323, compound

HRID 1610917Notes

Reaction equation

HRID 1610917 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[CH2:6][NH2:7].[C:15](Cl)(Cl)=[S:16].C(N(CC)CC)C>C(OCC)(=O)C>[N:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:15]=[S:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 222583273-Methoxy-4-methoxymethoxybenzylamine

Product 1

HCID 22258323HCID 22258323, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3-methoxy-4-methoxymethoxybenzylamine (5.3 g, 26.9 mmol) in ethyl acetate (50 mL) was added, via an addition funnel) to a solution of thiophosgene (2.15 mL, 28.2 mmol) and triethylamine (7.87 mL, 56.5 mmol) in ethyl acetate (30 mL) at 0° C. The resultant solution was stirred at ambient temperature overnight. The solution was washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel eluted with ethyl acetate/hexanes (1/9 to 3/7) to give the product, 4-isothiocyanatomethyl-2-methoxy-1-methoxymethoxy-benzene, as a waxy tan solid, 4.9 g (76%). 1H NMR (CDCl3): δ 3.51 (s, 3H), 3.91 (s, 3 H), 4.64 (s, 2 H), 5.23 (s, 2 H), 6.83 (m, 2 H) and 7.14 (d, J=8 Hz).

Workup

  1. washThe solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluted with ethyl acetate/hexanes (1/9 to 3/7)

Sources & evidence

ORD record
ord-6338e06d351a4c5fac88fc39175bbbdd
Source dataset
uspto-grants-2006_01
Patent number
US06984647B2

Reaction notes

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