Water → 2-Benzylsulfanyl-benzothiazole

HRID 1590165Notes

Reaction equation

HRID 1590165 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[SH:10].C(N(CC)CC)C.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([S:10][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 178418395HCID 178418395, compound

Product 1

HCID 4974652-Benzylsulfanyl-benzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-benzothiazolthiol (250 g) in N,N-dimethylformamide (1 l) was added triethylamine (208 ml) under ice-cooling and dropwise a solution of benzyl bromide (178 ml) in N,N-dimethylformamide (300 ml) and the mixture was stirred for 40 minutes. The resulting solution was poured into water (10 l) and the formed precipitate was separated by filtration and dissolved in dichloromethane (3 l). After drying over anhydorous magnesium sulfate, dichloromethane was removed in vacuo to give 378 g of the objective compound.

Workup

  1. temperaturecooling
  2. customthe formed precipitate was separated by filtration
  3. dissolutiondissolved in dichloromethane (3 l)
  4. dry with materialAfter drying over anhydorous magnesium sulfate, dichloromethane
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-d8fc01cac543427cb507baee2651e475
Source dataset
uspto-grants-1993_04
Patent number
US05202339

Reaction notes

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