Water → 6-Methyl[2,6'-bi-1,3-benzothiazol]-2'-amine

HRID 2223996Notes

Reaction equation

HRID 2223996 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:18]([S-:20])#[N:19].[K+].BrBr.O>CN(C=O)C>[NH2:19][C:18]1[S:20][C:3]2[CH:4]=[C:5]([C:8]3[S:9][C:10]4[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=4[N:12]=3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7087Dehydrothio-4-toluidineHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 179535086-Methyl[2,6'-bi-1,3-benzothiazol]-2'-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(4-aminophenyl)-6-methyl-benzothiazole 1 (4.0 g, 16.6 mmol) and KSCN (2.6 g, 26.7 mmol) were dissolved in DMF (20 ml) and cooled in an ice-bath. Br2 (0.9 ml, 17 mmol) in DMF (15 ml) was added dropwise under 3 h. The mixture was stirred for another 20 h. Water was added and the precipitate formed was collected by filtration and dried. The crude product was triturated on the sinter with several portions of boiling dichloromethane to afford 2 as a light green-yellow solid (1.97 g, 40%). Mp 250-251° C.; 1H NMR (DMSO): δ 2.45 (3H, s, Ar—CH3), 7.34 (1H, d, J=8.4, ArH), 7.50 (1H, d, J=8.4, ArH), 7.89 (1H, d, J=8.4, ArH), 7.91 (1H, s, ArH), 7.99 (1H, d, J=8.4, ArH), 8.51 (1H, s, ArH), 8.56 (2H, s, NH2); 13C NMR (DMSO): δ 21.10, 116.7, 120.7, 121.8, 122.1, 125.6, 126.9, 128.1, 129.7, 133.3, 134.5, 135.0, 151.7, 165.9, 169.3; HR-FAB-MS m/z Found: 298.0521 C15H12N3S2 (M+H+): requires M, 298.0473.

Workup

  1. temperaturecooled in an ice-bath
  2. customthe precipitate formed
  3. filtrationwas collected by filtration
  4. customdried
  5. customThe crude product was triturated on the sinter with several portions of boiling dichloromethane

Sources & evidence

ORD record
ord-ef6002a5fd064d7da17650ac3491d286
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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