Tizanidine → HCID 86658847, compound

HRID 451350Notes

Reaction equation

HRID 451350 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3]([OH:5])=[O:4].[CH:7]1[C:12]2=[N:13][S:14][N:15]=[C:11]2[C:10]([NH:16][C:17]2[NH:21][CH2:20][CH2:19][N:18]=2)=[C:9]([Cl:22])[CH:8]=1.C(OCC)(=O)C>C(O)(C)C>[CH:7]1[C:12]2=[N:13][S:14][N:15]=[C:11]2[C:10]([NH:16][C:17]2[NH:21][CH2:20][CH2:19][N:18]=2)=[C:9]([Cl:22])[CH:8]=1.[Cl:1][CH:2]([Cl:6])[C:3]([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 5487TizanidineHCID 6597Dichloroacetic AcidHCID 8857Ethyl Acetate

Product 1

HCID 86658847HCID 86658847, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 3.0 g of dichloroacetic acid in 5 ml of isopropyl alcohol, 3.0 g of tizanidine base (99.15% HPLC) are added. After short heating to boil a solution results, from which, after addition of ethyl acetate, a crystalline precipitated product starts to separate. After cooling to 0 to 5° C. and aspiration 4.15 g tizanidine dichloroacetate are obtained.

Workup

  1. temperatureAfter short heating
  2. customresults, from which
  3. customa crystalline precipitated product starts to separate

Sources & evidence

ORD record
ord-a76f4316c1324e62a052afd0e8706580
Source dataset
uspto-grants-2013_07
Patent number
US08487113B2

Reaction notes

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