Chloroacetyl chloride → 2-Chloroacetylamino-6-amino-benzo[1,2-d:5,4-d']bisthiazole

HRID 67104

Reaction equation

HRID 67104 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[S:8][C:9]2[C:10](=[CH:12][C:13]3[N:14]=[C:15]([NH2:19])[S:16][C:17]=3[CH:18]=2)[N:11]=1>CN(C)C=O>[Cl:1][CH2:2][C:3]([NH:19][C:15]1[S:16][C:17]2[C:13](=[CH:12][C:10]3[N:11]=[C:7]([NH2:6])[S:8][C:9]=3[CH:18]=2)[N:14]=1)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 844005ST076754

Product 1

HCID 205282012-Chloroacetylamino-6-amino-benzo[1,2-d:5,4-d']bisthiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 gm of chloroacetyl chloride were added to a stirred solution of 2.2 gm of 2,6-diamino-benzo[1,2-d:5,4-d']bisthiazole in 20 ml of dimethylformamide at 5° C. The resulting suspension was heated for 1 hour on a waterbath, then cooled, and the solid 2,6-bis-(chloroacetyl-amino)-benzo[1,2-d:5,4-d']bisthiazole was filtered off. While stirring, 0.5 gm of an aqueous saturated sodium carbonate solution was added to the filtrate. After 1 hour the precipitate was filtered off, dissolved in 30 ml of dimethylformamide/dioxan (1:1), freed from traces of insoluble material and precipitated again with water. The crystals were dissolved in dimethylformamide and the solution was treated with an excess of 2 N hydrochloric acid. The hydrochloride obtained thereby was washed and dried.

Workup

  1. temperatureThe resulting suspension was heated for 1 hour on a waterbath
  2. temperaturecooled
  3. filtrationthe solid 2,6-bis-(chloroacetyl-amino)-benzo[1,2-d:5,4-d']bisthiazole was filtered off
  4. addition0.5 gm of an aqueous saturated sodium carbonate solution was added to the filtrate
  5. filtrationAfter 1 hour the precipitate was filtered off
  6. dissolutiondissolved in 30 ml of dimethylformamide/dioxan (1:1)
  7. customprecipitated again with water
  8. dissolutionThe crystals were dissolved in dimethylformamide
  9. additionthe solution was treated with an excess of 2 N hydrochloric acid

Sources & evidence

ORD record
ord-aef9ba5b12d9479fa5de664a8af7a853
Source dataset
uspto-grants-1982_08
Patent number
US04344946

Linked notes

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