Potassium Hydroxide → HCID 86056602, compound

HRID 2222192Notes

Reaction equation

HRID 2222192 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[S:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[K+]>C1COCC1>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:8]2[S:9][C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86599615HCID 86599615, compound

Product 1

HCID 86056602HCID 86056602, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.1 g (18 mmol) 2-(4-Chloro-phenylamino)-5-methyl-thiazole-4-carboxylic acid ethyl ester and 10.8 ml 5M aq. KOH in 50 ml THF was heated to 50° C. for 16 h. After evaporation of the volatiles 100 ml water and 6 ml HOAc was added and the mixture was extracted 3× with 500 ml ethyl acetate. The combined organic layers were washed 3× with 200 ml water and concentrated at 40° C. under reduced pressure until precipitation started. After cooling to room temperature the crystals were filtered off, washed 3× with 10 ml ethyl acetate and dried to yield 2.16 g (44.5%) of the title compound. MS (m/e): 453.0 (MH+, 100%)

Workup

  1. customAfter evaporation of the volatiles 100 ml water and 6 ml HOAc
  2. additionwas added
  3. extractionthe mixture was extracted 3× with 500 ml ethyl acetate
  4. washThe combined organic layers were washed 3× with 200 ml water
  5. concentrationconcentrated at 40° C. under reduced pressure until precipitation
  6. temperatureAfter cooling to room temperature the crystals
  7. filtrationwere filtered off
  8. washwashed 3× with 10 ml ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-d0b3a6ec3cd0464383c4e57cef0d1a3b
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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