Ammonia → HCID 178446961, compound

HRID 1741228Notes

Reaction equation

HRID 1741228 reaction equation
[Na].[NH3:2].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[C:12]([O:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:13]([C:26]#[N:27])[C:14](=[C:17]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]=1[Cl:19])[C:15]#[N:16]>C(O)CC>[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[C:12]([O:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:13]2[C:14](=[C:17]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]=1[Cl:19])[C:15](=[NH:16])[NH:27][C:26]2=[NH:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 11004994HCID 11004994, compound

Product 1

HCID 178446961HCID 178446961, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of sodium metal (0.7 g) in n-propyl alcohol (200 mL) was fed gaseous ammonia at a flow rate of 120 mL/min. at room temperature for 1 hour. Then, 22.8 g of 4-(2-aminophenylthio)-5-chloro-3,6-diisopentoxyphthalonitrile was added and the mixture was stirred at 50~60° C. for 20 hours. After cooling, n-propyl alcohol was distilled off and the residue was dissolved in 200 mL of toluene under warming at 30~40° C. Then, 500 mL of water was added and the mixture was stirred for dispersing and allowed to stand for phase separation. The above procedure was repeated 4 times to wash the toluene solution. The toluene was then distilled off and 200 mL of n-heptane was added. The mixture was stirred at 60~65° C. for 30 minutes and then cooled to room temperature. The resulting crystals were collected and dried to provide 20.3 g (yield 85.8%) of 5-(2-aminophenylthio)-6-chloro-1,3-diimino-4,7-diisopentoxyisoindoline. ##STR9##

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. temperatureAfter cooling
  4. distillationn-propyl alcohol was distilled off
  5. dissolutionthe residue was dissolved in 200 mL of toluene
  6. temperatureunder warming at 30~40° C
  7. additionThen, 500 mL of water was added
  8. stirringthe mixture was stirred
  9. additionfor dispersing
  10. customto stand for phase separation
  11. washto wash the toluene solution
  12. distillationThe toluene was then distilled off
  13. addition200 mL of n-heptane was added
  14. stirringThe mixture was stirred at 60~65° C. for 30 minutes
  15. customThe resulting crystals were collected
  16. customdried

Sources & evidence

ORD record
ord-ec4d84ac2c804921b835f1f84c33631c
Source dataset
uspto-grants-1999_10
Patent number
US05973140

Reaction notes

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