Sodium Hydroxide → HCID 13135253, compound

HRID 1632674Notes

Reaction equation

HRID 1632674 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([O:11][C:12]3[CH:25]=[CH:24][C:15]([O:16][CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>O>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([O:11][C:12]3[CH:25]=[CH:24][C:15]([O:16][CH:17]([CH3:23])[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13135252HCID 13135252, compound

Product 1

HCID 13135253HCID 13135253, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

37.8 g (0.1 mole) of ethyl 2-[4-(5- chlorothiazolo[5,4-b]pyridin-2-yloxy)-phenoxy]-propionate from Example 1 were stirred with 4.4 g (0.11 mole) of sodium hyroxide in 250 ml of water for 24 hours at approximately 30° C. The slightly cloudy solution was filtered, 500 ml of toluene were then added and the mixture was warmed to 80° C. and its pH was adjusted to 1 with concentrated hydrochloric acid. The phases were separated while hot, the water phase was again stirred thoroughly with 250 ml of toluene under hot conditions, and the combined toluene phases were dried azeotropically and concentrated to a volume of approximately 250 ml.

Workup

  1. filtrationThe slightly cloudy solution was filtered
  2. addition500 ml of toluene were then added
  3. customThe phases were separated while hot, the water phase
  4. dry with materialthe combined toluene phases were dried azeotropically
  5. concentrationconcentrated to a volume of approximately 250 ml

Sources & evidence

ORD record
ord-721a887e43db4cca99102bda7f6e561d
Source dataset
uspto-grants-1984_10
Patent number
US04477276

Reaction notes

Loading…