Ammonia → 5-(Benzyloxy)-7-bromobenzo[d]thiazol-2-amine

HRID 447056Notes

Reaction equation

HRID 447056 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([NH2:19])=[S:18])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr.N>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]2[S:18][C:17]([NH2:19])=[N:16][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 57813605(3-Benzyloxy-5-bromo-phenyl)thiourea

Product 1

HCID 578135885-(Benzyloxy)-7-bromobenzo[d]thiazol-2-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of (3-benzyloxy-5-bromo-phenyl)-thiourea (2.0 g, 5.93 mmol) in CHCl3 (80.0 mL) was cooled to −60° C. followed by drop wise addition of a solution of bromine (0.30 mL, 5.93 mmol) in CHCl3 (20.0 mL). The resulting reaction mixture was stirred at room temperature for 15 minutes followed by refluxing at 70° C. for 1 h. The reaction mass was then cooled and basified with 25% aqueous ammonia solution to pH 8-9 and then extracted with EtOAc (3×150.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified over silica gel (60-120 M, 40% EtOAc-Hexane) to get the desired compound (1.35 g, 68%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureby refluxing at 70° C. for 1 h
  3. temperatureThe reaction mass was then cooled
  4. extractionextracted with EtOAc (3×150.0 mL)
  5. dry with materialThe combined organics was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified over silica gel (60-120 M, 40% EtOAc-Hexane)

Sources & evidence

ORD record
ord-a7f68ecf79f646fa82c85010047a67e0
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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