2-Chlorobenzothiazole → HCID 22767696, compound

HRID 1111737Notes

Reaction equation

HRID 1111737 reaction equation
[C:1]1([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][NH:13][C:8]=1[CH:7]=[CH:6]2.[H-].[Na+].Cl[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1>CN(C)C=O>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:13]1[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[C:1]([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=3)[C:9]=2[CH:11]=[CH:12]1

Participants

5

Reactant 3

HCID 119872-Chlorobenzothiazole3×HCID 24758Sodium hydrideHCID 178508668HCID 178508668, compound

Product 1

HCID 22767696HCID 22767696, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3.98 g. 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine dissolved in 250 ml. dry dimethylformamide are added, with stirring under nitrogen, 1.15 g. ca. 50% sodium hydride-mineral oil dispersion. After stirring for 1.5 hours, 3.90 g. 2-chlorobenzothiazole are added and the mixture is heated at 95° for 3 hours. An additional 1.29 g. 2-chlorobenzothiazole are added and heating at 95° is continued for 11 hours. A third portion of 2-chlorobenzothiazole (1.29 g.) is added and heating at 95° is continued for 8 hours. The reaction mixture is processed as in Example 69 and the crude product is recrystallized (twice) from dimethylformamide and is thoroughly dried to yield 2.30 g. title compound, m.p. 326° (dec).

Workup

  1. stirringAfter stirring for 1.5 hours
  2. temperaturethe mixture is heated at 95° for 3 hours
  3. temperatureheating at 95°
  4. temperatureheating at 95°
  5. waitis continued for 8 hours
  6. customthe crude product is recrystallized (twice) from dimethylformamide
  7. customis thoroughly dried
  8. customto yield 2.30 g

Sources & evidence

ORD record
ord-4cf74bbc1272433091555757c33fd7c3
Source dataset
uspto-grants-1978_10
Patent number
US04118561

Reaction notes

Loading…