Hydrochloric Acid → HCID 17965904, compound

HRID 133690Notes

Reaction equation

HRID 133690 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[CH:24]=1)[C:9]([NH:11][C:12]1[S:13][C:14]([C:17]([O:19]CC)=[O:18])=[CH:15][N:16]=1)=[O:10].[OH-].[Na+].Cl>C1COCC1.O>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][O:25][C:23]1[CH:22]=[C:8]([CH:7]=[C:6]([O:5][CH2:4][C:3]2[CH:34]=[CH:35][CH:36]=[CH:37][C:2]=2[Cl:1])[CH:24]=1)[C:9]([NH:11][C:12]1[S:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][N:16]=1)=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59735873HCID 59735873, compound

Product 1

HCID 17965904HCID 17965904, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-[3,5-di-(2-chlorobenzyloxy)benzoyl]aminothiazole-5-carboxylate (158 mg, 0.28 mmol) in THF (2 ml) was treated with sodium hydroxide solution (0.57 ml of 2M, 1.4 mmol), and the reaction stirred at 40-50 deg C., until complete hydrolysis was achieved (with tlc monitoring, approximate reaction time 2 hrs). The resulting solution was cooled, diluted with water (5 ml) and acidified to pH1 using c.HCl. The precipitate thus formed was filtered off, washed (water) and dried to give the title compound as a colourless solid, 130 mg, 1H NMR δ (d6-DMSO): 5.25 (4H, s); 7.0 (1H, s); 7.4 (6H, m); 7.5 (2H, m); 7.6 (2H, m); 8.2 (1H, d).

Workup

  1. custom, until complete hydrolysis
  2. custom(with tlc monitoring, approximate reaction time 2 hrs)
  3. temperatureThe resulting solution was cooled
  4. customThe precipitate thus formed
  5. filtrationwas filtered off
  6. washwashed (water)
  7. customdried

Sources & evidence

ORD record
ord-d81def376953428c8d4af2ba3a83dded
Source dataset
uspto-grants-2008_06
Patent number
US07390908B2

Reaction notes

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