Hydrochloric Acid → HCID 14836845, compound

HRID 1111360Notes

Reaction equation

HRID 1111360 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)(=[O:5])=[O:4].[S-:20][C:21]#[N:22].[K+].BrBr.[ClH:26]>C(O)(=O)C.C(O)C>[ClH:26].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][N:8]1[C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]([F:17])([F:19])[F:18])=[CH:13][C:14]=2[S:20][C:21]1=[NH:22])(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24408BromineHCID 516872Potassium thiocyanateHCID 10565966HCID 10565966, compound

Product 1

HCID 14836845HCID 14836845, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The procedure is as in Example 3, starting with N-methyl-2-(p-trifluoromethoxyanilino)ethanesulphonamide (3.5 g), potassium thiocyanate (4.7 g) and bromine (2.2 g) in acetic acid (30 cc). After 18 hours at a temperature in the region of 20° C., neutralization with 30% strength sodium hydroxide and extraction with ethyl acetate, a crude product is obtained, which product is converted to a hydrochloride by adding 4.2N ethereal hydrogen chloride (3 cc) in ethanol (25 cc) and recrystallized in absolute ethanol (50 cc). The N-methyl-2-(2-imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanesulphonamide hydrochloride thereby obtained (2.1 g) melts at 242° C.

Workup

  1. extractionAfter 18 hours at a temperature in the region of 20° C., neutralization with 30% strength sodium hydroxide and extraction with ethyl acetate
  2. customa crude product is obtained
  3. customrecrystallized in absolute ethanol (50 cc)

Sources & evidence

ORD record
ord-53643c5589c5469f9748604c1b3ad395
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

Loading…