Sodium Hydroxide → [6-(2-Nitro-phenyl)-imidazo[2,1-b]thiazol-3-yl]-acetic acid

HRID 419924Notes

Reaction equation

HRID 419924 reaction equation
C(O[C:4]([C:6]1[N:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])[N:11]=[C:8]2[S:9][CH:10]=1)=O)C.[OH-:23].[Na+].C1[CH2:29][O:28]CC1.O>>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[N:11]=[C:8]2[N:7]([CH:13]=1)[C:6]([CH2:4][C:29]([OH:28])=[O:23])=[CH:10][S:9]2)([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21881883Oxolane--water (1/1)HCID 25232522Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate

Product 1

HCID 43464941[6-(2-Nitro-phenyl)-imidazo[2,1-b]thiazol-3-yl]-acetic acidYield 99%

Conditions

Temperature
50 °C

Procedure

6-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (466 mg, 1.47 mmol) in 2:1 THF/Water was combined with 4 eq of NaOH (234 mg). The reaction mixture was heated to 50° C. for 3 hours. The reaction mixture was concentrated to dryness, the residue dissolved in water (20 ml), washed with CH2Cl2, and the aqueous layer was adjusted to pH=3 with 4N HCl. The solids were collected by filtration, washed with water and air dried to obtain the acid product was a brown solid (442 mg, 99% yield) (MS, M++H=304.0)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue dissolved in water (20 ml)
  3. washwashed with CH2Cl2
  4. filtrationThe solids were collected by filtration
  5. washwashed with water and air
  6. customdried
  7. customto obtain the acid product

Sources & evidence

ORD record
ord-5d567369b25b4103a3168dc620b5b846
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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