4-Toluenesulfonyl chloride → HCID 22274441, compound

HRID 1064781Notes

Reaction equation

HRID 1064781 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][CH2:11][OH:12])=[CH:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][CH2:11][CH2:10][C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=3[CH:7]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 222746535-Bromobenzo[b]thiophene-2-ethanol

Product 1

HCID 22274441HCID 22274441, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 165C (0.5 g) in methylene chloride (10 mL) was added triethylamine (0.3 g, 1.5 eq) followed by tosyl chloride (0.37 g, 1.0 ea). The solution was stirred at RT overnight and washed with 3×20 mL of water. The methylene chloride layer was concentrated to viscous oil (0.98 g, 68.1% potency, 83.5% yield). The crude product can be purified by crystallization from 20:80 EtOAc:hexane to give crystalline solid (0.48 g). 1H NMR(CDCl3, δ) 2.38 (s, 3H), 3.21 (t, 2H), 4.30 (t, 2H), 6.87 (s, 1H), 7.18 (d, 2H), 7.36 (d of d, 1H), 7.55 (d, 1H), 7.63 (d, 2H), 7.75 (d, 1H). MS(m/z): 428, 430 (M+NH4).

Workup

  1. washwashed with 3×20 mL of water
  2. concentrationThe methylene chloride layer was concentrated to viscous oil (0.98 g, 68.1% potency, 83.5% yield)
  3. customThe crude product can be purified by crystallization from 20:80 EtOAc

Sources & evidence

ORD record
ord-1d160a2bc76a4bf3bbc53144608d7423
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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