Lithium Hydroxide → HCID 57971491, compound

HRID 913241Notes

Reaction equation

HRID 913241 reaction equation
[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[S:4][C:5]([C:8]([O:10]CC)=[O:9])=[CH:6][N:7]=1.[OH-].[Li+]>O1CCOCC1>[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[S:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67408155HCID 67408155, compound

Product 1

HCID 57971491HCID 57971491, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 2-[methyl(2-phenylethyl)amino]-1,3-thiazole-5-carboxylate (0.56 g, 1.93 mmol) in dioxane (10 mL) was added lithium hydroxide (5.8 mmol, 1.9 mL of a 3.0M solution) and the reaction was warmed to 75° C. for 2.5 hours. The reaction was partitioned between 1M HCl and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to give the title compound. 1H NMR (600 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.22 (m, 5H), 3.68 (t, J=7.33 Hz, 2H), 3.31 (bs, 1H), 2.99 (s, 3H), 2.87 (t, J=7.63 Hz, 2H); ESIMS calcd 263.1 (M++H), found 263.0 (M++H).

Workup

  1. customThe reaction was partitioned between 1M HCl and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-afd4f358713244ee8ef8eb45d2ba4b1a
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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