Triethylamine → HCID 178493205, compound

HRID 638233Notes

Reaction equation

HRID 638233 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1([F:37])[O:35][C:17]2=[CH:18][C:19]3[N:23]=[C:22]([S:24][CH2:25][C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][N:27]=4)[NH:21][C:20]=3[CH:34]=[C:16]2[O:15][CH:14]1[F:36].C(N(CC)CC)C>C(OCC)(=O)C.C(Cl)Cl>[F:37][C:13]1([F:12])[O:35][C:17]2=[CH:18][C:19]3[N:23]=[C:22]([S:24]([CH2:25][C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][N:27]=4)=[O:6])[NH:21][C:20]=3[CH:34]=[C:16]2[O:15][CH:14]1[F:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 178493196HCID 178493196, compound

Product 1

HCID 178493205HCID 178493205, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.81 g of approximately 85% pure m-chloroperoxybenzoic acid in 20 ml of ethyl acetate is added dropwise to a solution of 1.5 g of 6,6,7-trifluoro-6,7-dihydro-2-[(4-methoxy-2-pyridyl)methylthio]-1H-[1,4]-dioxino[2,3-f]benzimidazole in 50 ml of methylene chloride at -20° C. to -15° C. in the course of 30 min., with stirring, and stirring is continued at this temperature for 30 min. 0.66 ml of triethylamine is added and the organic solution is washed with 1M potassium bicarbonate solution and then with water, dried with magnesium sulfate and concentrated in vacuo. The residue is allowed to crystallize from ether. 1.2 g (77%) of the title compound of m.p. 166°-167° C. (decomposition), from ethyl acetate, are obtained.

Workup

  1. stirringstirring
  2. washthe organic solution is washed with 1M potassium bicarbonate solution
  3. dry with materialwith water, dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto crystallize from ether

Sources & evidence

ORD record
ord-d1df111f1d8044c69edf9d02e6370c1f
Source dataset
uspto-grants-1985_12
Patent number
US04560693

Reaction notes

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