Methyl p-toluenesulfonate → Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)

HRID 1070376Notes

Reaction equation

HRID 1070376 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][O:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>C(OCC)C>[S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)([O-:16])(=[O:15])=[O:13].[CH3:12][N+:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][C:3]=1[S:2][CH3:1]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 119892-(Methylthio)benzothiazole

Product 1

HCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)Yield 116.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-methylthio-benzothiazole (18.4 g, 0.1 mol) and methyl-p-toluenesulfonate (76 mL, 0.5 mol) was heated to a temperature between 120° C. to 145° C. for 1 hour. After cooling to room temperature diethyl ether (200 mL) was added. The resulting solid was triturated with diethyl ether and isolated by filtration to give the crude product (42.7 g, quantitative). 1H-NMR (300 MHz, CDCl3): δ 8.12 (d, 1H), 7.92 (d, 1H), 7.62 (d, 3H), 7.3 (t, 1H), 7.02 (d, 2H), 4.05 (s, 3H); 3.0 (s, 3H), 2.23 (3, 3H).

Workup

  1. temperaturewas heated to a temperature between 120° C. to 145° C. for 1 hour
  2. additionwas added
  3. customThe resulting solid was triturated with diethyl ether
  4. customisolated by filtration

Sources & evidence

ORD record
ord-493c68651b8b431eab76b2f635f2e68a
Source dataset
uspto-grants-2005_06
Patent number
US06902900B2

Reaction notes

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