Water → N-(1H-benzimidazol-2-yl)-1,3-benzothiazol-2-amine

HRID 44124Notes

Reaction equation

HRID 44124 reaction equation
[2H][C:2]1[C:7]([2H])=[C:6]([NH2:9])[C:5]([NH2:10])=[C:4]([2H])[C:3]=1[2H].C[SH-][C:15]([SH-]C)=[N:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.O>CN(C=O)C>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[NH:16][C:15]1[NH:9][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107729501,2-Diaminobenzene (D4, 98%)HCID 178504144HCID 178504144, compound

Product 1

HCID 15578107N-(1H-benzimidazol-2-yl)-1,3-benzothiazol-2-amineYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
153 °C

Procedure

O-phenylenediamine (21.6 g (0.2 mol)) was dissolved in 944 g of DMF, and thereto was added dropwise a solution obtained by dissolving 50.9 g (0.20 mol) of S,S′-dimethyl-N-(2-benzothiazolyl)-carbonimidodithioate in 1258 g of DMF. The resulting mixture was then heated to 153° C., refluxed under a nitrogen atmosphere for 13 hours, and then cooled to 0° C. Thereto was added dropwise 2000 g of water, and a precipitate was filtered off, washed with water, and dried to obtain 32.0 g of 2-(2-benzothiazolylamino)benzoimidazole (L8: see Table 1 below). The yield was 60.1% based on o-phenylenediamine.

Workup

  1. additionwas added dropwise a solution
  2. customobtained
  3. temperaturerefluxed under a nitrogen atmosphere for 13 hours
  4. temperaturecooled to 0° C
  5. filtrationa precipitate was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-fac1acc8c38b43438104ddd3a7536cf4
Source dataset
uspto-grants-2013_09
Patent number
US08540904B2

Reaction notes

Loading…