Ammonia → HCID 86736148, compound

HRID 1703777Notes

Reaction equation

HRID 1703777 reaction equation
[CH2:1]([C:15]1[CH:27]=[CH:26][C:18]([N:19]([CH2:23][CH2:24][OH:25])[CH2:20][CH2:21][OH:22])=[CH:17][CH:16]=1)[C:2]1[CH:14]=[CH:13][C:5]([N:6]([CH2:10][CH2:11][OH:12])[CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[S].[NH3:29].[Cl-:30].[NH4+]>C(O)(C)C.C(OCC)C.C(O)CO>[ClH:30].[C:1]([C:15]1[CH:16]=[CH:17][C:18]([N:19]([CH2:23][CH2:24][OH:25])[CH2:20][CH2:21][OH:22])=[CH:26][CH:27]=1)([C:2]1[CH:3]=[CH:4][C:5]([N:6]([CH2:10][CH2:11][OH:12])[CH2:7][CH2:8][OH:9])=[CH:13][CH:14]=1)=[NH:29]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 2923202,2',2'',2'''-[methanediylbis(benzene-4,1-diylnitrilo)]tetraethanolHCID 5362487Sulfur

Product 1

HCID 86736148HCID 86736148, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 486.8 grams (1.3 moles) of 4,4'-methylenebis[N,N-bis(2-hydroxyethyl)aniline], 230 grams (7.2 moles) of sulfur and 800 grams of ethylene glycol was heated at 140° C. for 4 hours while a stream of ammonia gas was bubbled therein. To the reaction mixture was then added 170 grams (3.2 moles) of ammonium chloride and heating at 140° C. was continued for an additional 16 hours. The reaction mixture was cooled to 60° C., diluted with 3 liters of isopropanol, and added to diethyl ether to precipitate the dye. The dye was recovered by filtration, dissolved in 70° C. water and salted out by adding sodium chloride thereto. The resulting product was recovered and dried in vacuo. The dried tar was dissolved in 500 mls. of N,N-dimethylformamide, treated with activated carbon, filtered and precipitated by adding the filtrate to diethyl ether. This was repeated using 500 mls. of methanol. The resulting oil was recovered and triturated with isopropanol and diethyl ether to effect crystallization. The crystals were dried in vacuo to obtain 95 grams of product, which was found to be pure by thin layer chromatography.

Workup

  1. customwas bubbled
  2. temperatureThe reaction mixture was cooled to 60° C.
  3. customto precipitate the dye
  4. filtrationThe dye was recovered by filtration
  5. dissolutiondissolved in 70° C. water
  6. additionby adding sodium chloride
  7. customThe resulting product was recovered
  8. customdried in vacuo
  9. dissolutionThe dried tar was dissolved in 500 mls
  10. additionof N,N-dimethylformamide, treated with activated carbon
  11. filtrationfiltered
  12. customprecipitated
  13. additionby adding the filtrate to diethyl ether
  14. customThe resulting oil was recovered
  15. customtriturated with isopropanol and diethyl ether
  16. customcrystallization
  17. customThe crystals were dried in vacuo

Sources & evidence

ORD record
ord-de42e30d54dd496bb4afcb83e0ee9044
Source dataset
uspto-grants-1978_11
Patent number
US04125557

Reaction notes

Loading…