Sodium Hydroxide → 3-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzamide

HRID 1408811Notes

Reaction equation

HRID 1408811 reaction equation
C([NH:5][C:6]1[S:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[CH:18]=3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:11]2)[N:10]=1)(C)(C)C.[OH-:34].[Na+]>Cl>[NH2:5][C:6]1[S:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]([NH2:24])=[O:34])[CH:18]=3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:11]2)[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671746273-(2'-(tert-butylamino)-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzonitrile

Product 1

HCID 584244103-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-(2′-(tert-butylamino)-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzonitrile (30 mg, 0.066 mmol) in concentrated HCl (5 mL) was stirred at 100 for 2 h. Aqueous NaOH (6 N) was added until pH=8. The mixture was extracted with EtOAc and the organic layer was dried and concentrated to give the residue, which was purified by preparative TLC to give 3-(2′-amino-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzamide (20 mg, 73%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customto give the residue, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-d61fdac86fc84922982f3cf323c99104
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

Loading…