Glycol monoethyl ether → HCID 178492518, compound

HRID 1730798Notes

Reaction equation

HRID 1730798 reaction equation
C(OCCO)C.[S-2].[Na+].[Na+].[Na].[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:14]=1[CH:15](S)[NH:16][C:17]2=[NH:24].C1(S([O-])(=O)=O)C=CC=CC=1.[NH:36]=[C:37]1[NH2+:41][C:40](=[NH:42])[CH2:39][S:38]1>>[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:14]=1[C:15](=[C:39]1[S:38][C:37](=[NH:36])[NH:41][C:40]1=[NH:42])[NH:16][C:17]2=[NH:24]

Participants

6

Reactant 5

HCID 8076Glycol monoethyl etherHCID 14804Sodium SulfideHCID 5360545SodiumHCID 867342112,4-Diiminothiazolidinium benzenesulfonateHCID 178492520HCID 178492520, compound

Product 1

HCID 178492518HCID 178492518, compound

Conditions

Temperature
25 °C

Procedure

To 140 parts of 2-ethoxyethanol stirred at 100° C under an atmosphere of nitrogen there was added 8.6 parts of 60 percent active solid sodium sulfide and the resultant solution was filtered to remove undissolved material. The filtrate was mixed with 94 parts of dimethylformamide and 11.3 parts of 3,6-dimethoxy-phthalonitrile and the mixture stirred at 25° C for a period of 1 hour. The reaction mixture was then heated to 95° C over a period of 1 hour, cooled to 25° C and filtered to remove undissolved material which was found to be (4.5 parts) unreacted 3,6-dimethoxyphthalonitrile. The filtrate, which contained approximately 0.04 mole of the sodium salt of 4,7-dimethoxy-1-imino-3-mercaptoisoindoline was stirred and there was added 10.7 parts of 2,4-diiminothiazolidinium benzenesulfonate. Stirring was continued overnight at 25° C. The product which separated was collected by filtration, washed successively with four portions of 12.0 parts each of methyl alcohol and finally dried in vacuo to obtain 4.5 parts of 4,7-dimethoxy-1-imino-3-(2,4-diimino-5-thiazolidinylidene)isoindoline as a red solid which melted at 227°-246° C (dec).

Workup

  1. filtrationthe resultant solution was filtered
  2. customto remove undissolved material
  3. additionThe filtrate was mixed with 94 parts of dimethylformamide and 11.3 parts of 3,6-dimethoxy-phthalonitrile
  4. temperatureThe reaction mixture was then heated to 95° C over a period of 1 hour
  5. temperaturecooled to 25° C
  6. filtrationfiltered
  7. customto remove undissolved material which
  8. stirringwas stirred
  9. stirringStirring
  10. waitwas continued overnight at 25° C
  11. customThe product which separated
  12. filtrationwas collected by filtration
  13. washwashed successively with four portions of 12.0 parts each of methyl alcohol
  14. customfinally dried in vacuo

Sources & evidence

ORD record
ord-d3643d62fe1a4f2fac40adb2ae18938f
Source dataset
uspto-grants-1976_11
Patent number
US03993658

Reaction notes

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