Triethylamine → HCID 22403359, compound

HRID 2106952Notes

Reaction equation

HRID 2106952 reaction equation
[S:1]1[C:5]2[C:6]([C:10](Cl)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH3:13][Si:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:13][Si:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][O:17][C:10]([C:6]1[C:5]2[S:1][N:2]=[N:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

HCID 22403359HCID 22403359, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.99 g (0.01 mol) of 7-benzothiadiazolecarboxylic acid chloride in 18 ml of toluene are added dropwise over a period of 25 minutes to a solution of 1.9 ml (0.013 mol) of 2-trimethylsilylethanol, 2.4 ml (0.017 mol) of triethylamine and 18 ml of toluene. The reaction mixture is then stirred for 16 hours at room temperature and afterwards poured onto ice/water and extracted twice with ethyl acetate. The extracts are combined, washed with water, dried over magnesium sulfate, filtered and concentrated and the same amount of hexane is added and the batch is filtered through silica gel. Concentration gives 2.0 g (71% of the theoretical yield) of product; m.p. 37°-39° C.

Workup

  1. additionafterwards poured onto ice/water
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionthe same amount of hexane is added
  8. filtrationthe batch is filtered through silica gel
  9. concentrationConcentration
  10. customgives 2.0 g (71% of the
  11. customtheoretical yield) of product

Sources & evidence

ORD record
ord-417cfdb116f548efa209a71da99d8700
Source dataset
uspto-grants-1990_06
Patent number
US04931581

Reaction notes

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