Methanesulfonic Acid → 2-(4-Aminophenyl)benzothiazole methanesulphonic acid salt

HRID 363303Notes

Reaction equation

HRID 363303 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH3:17][S:18]([OH:21])(=[O:20])=[O:19]>C(OCC)(=O)C>[CH3:17][S:18]([OH:21])(=[O:20])=[O:19].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 2344752-(4-Aminophenyl)benzothiazole

Product 1

HCID 877273232-(4-Aminophenyl)benzothiazole methanesulphonic acid saltYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-aminophenyl)benzothiazole (0.5 g, 2.21 mmol) in ethyl acetate (65 ml) was added dropwise methanesulphonic acid (0.215 g, 2.21 mmol) at room temperature. The reaction mixture was stirred for 30 minutes. The product was collected and washed with hot ethyl acetate to give a pale yellow powder (0.67 g, 94%), m.p. 261°-262° C.; vmax /cm-1 3422, 2880, 2633, 1598, 1487, 1322, 1220, 1149, 1043, 967, 780, 755, 561; δH (DMSO-d6) 8.10(1H, d, J7.9, 4-H), 8.00(3H, m, 7, 2', 6'-H), 7.52(1H, t, J7.3, 5-H), 7.42(1H, t, J7.5, 6-H), 7.06(2H, d, J8.5, 3', 5'-H), 5.72(3H, br s, NH3+), 2.41(3H, s, CH3).

Workup

  1. customThe product was collected
  2. washwashed with hot ethyl acetate

Sources & evidence

ORD record
ord-5c0dc69af73046c59c49b435471033a0
Source dataset
uspto-grants-1999_02
Patent number
US05874431

Reaction notes

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