Ethylenediamine → AGN-PC-0NICCC

HRID 1604981Notes

Reaction equation

HRID 1604981 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]#[N:12])=[N:2]1.[CH2:13](N)[CH2:14][NH2:15].C(=S)=S.C(Cl)(Cl)[Cl:21]>>[ClH:21].[NH:12]1[CH2:13][CH2:14][N:15]=[C:11]1[CH2:10][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][N:2]=1

Participants

5

Reactant 4

HCID 3301EthylenediamineHCID 6212ChloroformHCID 6348Carbon DisulfideHCID 3236401,2-Benzisoxazole-3-acetonitrile

Product 1

HCID 12279087AGN-PC-0NICCC

Procedure

A mixture of 1,2-benzisoxazole-3-acetonitrile (1.6 g), ethylenediamine (0.7 g) and carbon disulfide (0.2 ml) was heated at 130° to 150°C for 0.5 hour and then allowed to stand at room temperature overnight. to the reaction mixture was added chloroform and the insoluble substance was filtered off. The filtrate was subjected to silica gel column chromatography and eluted with 10 to 20 % methanol-chloroform. The eluates were collected and treated with ethanolic hydrochloric acid to give the hydrochloride. The product was treated with charcoal and then recrystallized from ethanol to give the desired compound (0.4 g). m.p. 223° to 228°C.

Workup

  1. temperaturewas heated at 130° to 150°C for 0.5 hour
  2. filtrationthe insoluble substance was filtered off
  3. washeluted with 10 to 20 % methanol-chloroform
  4. customThe eluates were collected
  5. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-9d4bb807d28d4ad093f6ee52073c8e34
Source dataset
uspto-grants-1976_04
Patent number
US03948928

Reaction notes

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