Sodium Hydroxide → HCID 12905315, compound

HRID 904053Notes

Reaction equation

HRID 904053 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8](O)=O)([O-:3])=[O:2].[NH2:16][NH:17][C:18]([NH2:20])=[S:19].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>O.O1CCOCC1>[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[O:6][CH:7]([C:8]1[S:19][C:18]([NH2:20])=[N:17][N:16]=1)[CH3:11])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 2798552-(2-nitrophenoxy)propanoic acidHCID 2723789Thiosemicarbazide

Product 1

HCID 12905315HCID 12905315, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 100 milliliter, 3-neck flask adapted with a Claisen adaptor, paddle stirrer, thermometer, an addition funnel and condenser, was charged with 8.4 grams (0.040 moles) of 2-(2-nitrophenoxy)propanoic acid, (3.6 grams, 0.040 mole) of thiosemicarbazide and 30 ml. of dioxane. The slurry was heated to 90° centigrade and the addition funnel was charged with phosphorous oxychloride (POCl3). The POCl3 (6.7 grams, 0.044 mole) was slowly added (for 26 minutes) while maintaining the temperature within 90°-95° C., and then stirred for an additional 20 minutes. It was refluxed for 60 minutes and cooled. The flask was evacuated by using a water aspirator to remove volatiles (HCl, POCl3 and some dioxane), leaving a viscous gummy residue to which 50 ml. of water was added and the slurry was made basic by adding 50 percent solution of NaOH until the pH of the solution was 10, and a solid precipate formed. The solid precipate was filtered off, washed with water, dried in a vacuum oven at 80 degrees Centigrade to tan crystals, 5-(1-(2-nitrophenoxy) ethyl)-2-amino-1,3,4-thiadiazole. (Melting point 137-142 degrees Centigrade).

Workup

  1. temperatureThe slurry was heated to 90° centigrade
  2. temperaturewhile maintaining the temperature within 90°-95° C.
  3. temperatureIt was refluxed for 60 minutes
  4. temperaturecooled
  5. customThe flask was evacuated
  6. customto remove volatiles (HCl, POCl3
  7. customsome dioxane), leaving a viscous gummy residue to which 50 ml
  8. customa solid precipate formed
  9. filtrationThe solid precipate was filtered off
  10. washwashed with water
  11. dry with materialdried in a vacuum oven at 80 degrees Centigrade to tan crystals, 5-(1-(2-nitrophenoxy) ethyl)-2-amino-1,3,4-thiadiazole

Sources & evidence

ORD record
ord-de728e627e3e4636ade746a9cb2dbdbd
Source dataset
uspto-grants-1980_10
Patent number
US04230480

Reaction notes

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