Hydrochloric Acid → HCID 66847284, compound

HRID 529748Notes

Reaction equation

HRID 529748 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:16]([O:18]CC)=[O:17])=[C:5]([C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][CH3:15])[N:6]=1.[OH-].[K+].Cl.C(Cl)Cl>C1COCC1.O>[Br:1][C:2]1[S:3][C:4]([C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][CH3:15])[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 66847306HCID 66847306, compound

Product 1

HCID 66847284HCID 66847284, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate (1.40 g, 3.72 mmol), potassium hydroxide (278 mg) in THF (40 mL) and water (10 mL) was stirred for 20 hours at ambient temperature. The mixture was treated with 1M HCl aq. (ca. 8 mL, 2 eq.), DCM was added, and the organics separated and evaporated to dryness to give 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylic acid (1.23 g, 95%) as a yellow solid. LCMS (method 2) [M+H]+=350.1, RT=3.28 min. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 7.47 (dd, 1H), 7.39 (d, 1H), 7.13 (d, 1H), 3.73 (s, 3H).

Workup

  1. additionwas added
  2. customthe organics separated
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3e508ac1b36c43909b8200a8a7e1a640
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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