Triethylamine → HCID 86656160, compound

HRID 1192467Notes

Reaction equation

HRID 1192467 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12](O)[CH3:13].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:27]([CH:12]([C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH3:11])=[N:8][C:7]=2[C:2]=1[Br:1])[CH3:13])=[N+:28]=[N-:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 67258278HCID 67258278, compound

Product 1

HCID 86656160HCID 86656160, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(4-bromo-2-methyl-1,3-benzothiazol-5-yl)ethanol (1.81 g, 6.65 mmol) in methylene chloride (40 mL) was added triethylamine (1.39 mL, 9.98 mmol), followed by methanesulfonyl chloride (0.643 mL, 8.31 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The crude mesylate was dissolved in N,N-dimethylformamide (20 mL) and treated with sodium azide (2.16 g, 33.2 mmol) at room temperature overnight. After diluting with ethyl acetate, the mixture was washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was used in next step (1.90 g, 96%). LCMS calculated for C10H10BrI\T4S(M+H)+: m/z=297.0; found: 297.0.

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe crude mesylate was dissolved in N,N-dimethylformamide (20 mL)
  5. washthe mixture was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-99d2733ad759412da4cbf94ba318402d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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