Hydrochloric Acid → HCID 87219099, compound

HRID 1360852Notes

Reaction equation

HRID 1360852 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[S:20][C:19]([NH:21]C(=O)OC(C)(C)C)=[N:18][CH:17]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.ClCCl>[N:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[S:20][C:19]([NH2:21])=[N:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 87219503HCID 87219503, compound

Product 1

HCID 87219099HCID 87219099, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 ml of a 4M gaseous hydrochloric acid solution in ethyl acetate are added to 1 g of tert-butyl 5-{2-[(4-pyridinyloxy)methyl]phenyl}-1,3-thiazol-2-ylcarbamate, obtained in step 7.3, in 20 ml of dichloromethane. The mixture is left for 4 hours at room temperature. The reaction medium is concentrated and it is brought to a basic pH with a 5% sodium hydrogen sulfate solution. The precipitate formed is filtered and chromatographed on a silica gel column, eluting with a dichloromethane/methanol 95/5 (V/V) mixture to give 0.58 g of a beige foam.

Workup

  1. concentrationThe reaction medium is concentrated
  2. customThe precipitate formed
  3. filtrationis filtered
  4. customchromatographed on a silica gel column
  5. washeluting with a dichloromethane/methanol 95/5 (V/V) mixture

Sources & evidence

ORD record
ord-ef022355b72b4f96b0c9c3f3c8506333
Source dataset
uspto-grants-2011_02
Patent number
US07879889B2

Reaction notes

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