Bromine → 2-Bromo-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene

HRID 1051429Notes

Reaction equation

HRID 1051429 reaction equation
[CH3:1][C:2]1[C:13]2[N:9]([C:10]([CH2:15][CH2:16][CH3:17])=[N:11][C:12]=2[CH3:14])[C:8]2[N:7]=[CH:6][S:5][C:4]=2[N:3]=1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][C:6]1[S:5][C:4]2[N:3]=[C:2]([CH3:1])[C:13]3[N:9]([C:10]([CH2:15][CH2:16][CH3:17])=[N:11][C:12]=3[CH3:14])[C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 734258565,6-Dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene2×

Product 1

HCID 867155612-Bromo-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indaceneYield 30%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene from example 1 (40 mg, 0.16 mmol) in CHCl3 (10 mL) was added Br2 (78 mg, 0.5 mmol), then the solution was stirred at room temperature overnight to give a brown solution. LC-MS showed 30% of the title compound and 35% of 5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene. The reaction mixture was diluted with sat. NaHSO3 solution. The aqueous layer was extracted with DCM (3×10 mL). The combined organic layers were dried with Na2SO4, filtered and concentrated.

Workup

  1. customto give a brown solution

Sources & evidence

ORD record
ord-77f19434d8cb4885b985dbc040bfc8f8
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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