Hydrochloric Acid → HCID 86690815, compound

HRID 1465516Notes

Reaction equation

HRID 1465516 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7]C(=O)C)=[N:4][C:3]=1[C:11]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][C:12]=1[CH3:27].Cl.[OH-].[Na+]>CO>[Br:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:11]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][C:12]=1[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690816HCID 86690816, compound

Product 1

HCID 86690815HCID 86690815, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol solution (10.0 mL) containing N-{5-bromo-4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl}acetamide (2-3, 465 mg, 1.3 mmol) and 6 N hydrochloric acid (6.0 mL) was heated at reflux for 4.0 h. The solution was added with 10% aqueous NaOH and the resultant solids were collected to give 5-bromo-4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (2-4, 325 mg) as white solids in 55% yield: 1H NMR (500 MHz, DMSO-d6) δ 6.97-7.04 (m, 4H), 6.65 (s, 2 H), 3.76 (s, 3 H), 2.03 (s, 6 H). ESI-MS: m/z 405.3, 407.2 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.0 h
  3. customthe resultant solids were collected

Sources & evidence

ORD record
ord-58d5b8bc56f14ec09730d0771e64a0c8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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