Methanol → HCID 67081740, compound

HRID 1188745Notes

Reaction equation

HRID 1188745 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[SH:19].CO>C1(C)C=CC=CC=1>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[SH:19].[I:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[S:19][C:12]3[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2355092-Amino-5-methoxybenzene-1-thiolHCID 8172111-(Chloromethyl)-4-iodobenzene

Product 2

HCID 2355092-Amino-5-methoxybenzene-1-thiolHCID 67081740HCID 67081740, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-5-methoxythiophenol was prepared as set forth in C. A. Mathis, Y. Wang, D. P. Holt, G-F. Huang, M. L. Debnath and W. E. Klunk, “Synthesis and Evaluation of 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents.” J. Med. Chem., 46, pp 2740-2754 (2003). 4-Iodobenzyl chloride (5.0 g, 18.8 mmol) was added to a hot solution of 2-amino-5-methoxythiophenol (2.32 g, 15.0 mmol) in toluene (75 mL) and the reaction mixture was stirred at 100° C. for 1 h. Methanol (1 mL) was then added to destroy the excess 4-iodobenzoyl chloride. The hot toluene solution was then passed through a pad of silica gel (˜15 g) in a Buchner funnel. The silica gel was rinsed a few more times with hot toluene. The filtrate upon concentration gave pure 2-(4-iodophenyl)-6-methoxy-1,3-benzothiazole (4) (1.65 g, 40%) as off-white crystals.

Workup

  1. customto destroy the excess 4-iodobenzoyl chloride
  2. washThe silica gel was rinsed a few more times with hot toluene
  3. concentrationThe filtrate upon concentration

Sources & evidence

ORD record
ord-6fb19dd3d49c4560a89a8a1f4a7284af
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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