Ammonia → HCID 178467986, compound

HRID 1741230Notes

Reaction equation

HRID 1741230 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][O:31][CH2:32][CH3:33])=[C:13]([C:26]#[N:27])[C:14](=[C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[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][O:31][CH2:32][CH3:33])=[C:13]2[C:14](=[C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[C:18]=1[Cl:19])[C:15](=[NH:2])[NH:16][C:26]2=[NH:27]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 54010642HCID 54010642, compound

Product 1

HCID 178467986HCID 178467986, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of sodium metal (0.8 g) in n-propyl alcohol (250 mL) was fed gaseous ammonia at a flow rate of 120 mL/min. at room temperature for 1 hour. Then, 27.6 g of 4-(2-aminophenylthio)-5-chloro-3,6-di-(2-ethoxyethoxy) phthalonitrile was added and the mixture was stirred at 50~60° C. for 20 hours. After cooling, the reaction mixture was worked up in the same manner as in Example 1 to provide 27.6 g (yield 96.2%) of 5-(2-aminophenylthio)-6-chloro-1,3-diimino-4,7-di-(2-ethoxyethoxy) isoindoline of the following chemical formula. ##STR11##

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-36193f3dadff48f3b2df124745c667bb
Source dataset
uspto-grants-1999_10
Patent number
US05973140

Reaction notes

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