Hydrogen Bromide → 2-(3-Isopropylphenylamino)benzo[d]thiazol-5-ol

HRID 30802Notes

Reaction equation

HRID 30802 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Br.C(=O)([O-])[O-].[Na+].[Na+]>>[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 86045335N-(3-isopropylphenyl)-5-methoxybenzo[d]thiazol-2-amine

Product 1

HCID 860453372-(3-Isopropylphenylamino)benzo[d]thiazol-5-ol

Procedure

N-(3-isopropylphenyl)-5-methoxybenzo[d]thiazol-2-amine was charged with hydrobromic acid (45%) and subjected to microwave at 170° C. for 10 minutes. Reaction was then neutralized with sodium carbonate (saturated solution) and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to give 2-(3-isopropylphenylamino)benzo[d]thiazol-5-ol. HPLC=4.63 min; MS: MH+=285.

Workup

  1. customReaction
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e4599246945a4144906eb52c4becf9e1
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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