Acetonitrile → HCID 13983406, compound

HRID 580487Notes

Reaction equation

HRID 580487 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[S:3][CH2:2]1.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][C:14]([Cl:20])=[CH:15][CH:16]=2)[N:11]=1.C(#N)C>O>[Cl:20][C:14]1[N:13]=[C:12]2[C:17]([CH:18]=[CH:19][C:10]([NH:9][C:6]([C:4]3[S:3][CH2:2][S:1][CH:5]=3)=[O:8])=[N:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 122458441,3-DITHIOLE-4-CARBOXYLIC ACID

Product 1

HCID 13983406HCID 13983406, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 1,3-dithiole-4-carboxylic acid (4.6 g), N,N'-carbonyldiimidazole (7.5 g) and 2-amino-7-chloro-1,8-naphthyridine (4.2 g). The product obtained by precipitation in water (4.8 g) is taken up with boiling acetonitrile (300 cc), the insoluble material is removed by filtration, and the filtrate is poured into water (500 cc). The precipitate obtained is purified by recrystallization in an acetonitrile/water (5:2 by volume) mixture (650 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)- 1,3-dithiole-4-carboxamide (2.8 g), m.p. 235° C., is thereby obtained.

Workup

  1. customthe insoluble material is removed by filtration
  2. additionthe filtrate is poured into water (500 cc)
  3. customThe precipitate obtained
  4. customis purified by recrystallization in an acetonitrile/water (5:2 by volume) mixture (650 cc)

Sources & evidence

ORD record
ord-22888311a86a49e5932e16ba4f24777e
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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