Hydrochloric Acid → HCID 14836847, compound

HRID 1111361Notes

Reaction equation

HRID 1111361 reaction equation
[CH2:1]([NH:3][S:4]([CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)(=[O:6])=[O:5])[CH3:2].[S-:21][C:22]#[N:23].[K+].BrBr.[ClH:27]>C(O)(=O)C.C(O)C>[ClH:27].[CH2:1]([NH:3][S:4]([CH2:7][CH2:8][N:9]1[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:18])[F:19])=[CH:12][C:11]=2[S:21][C:22]1=[NH:23])(=[O:5])=[O:6])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24408BromineHCID 516872Potassium thiocyanateHCID 19828055HCID 19828055, compound

Product 1

HCID 14836847HCID 14836847, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The procedure is as in Example 3, starting with N-ethyl-2-(p-trifluoromethoxyanilino)ethanesulphonamide (6.1 g), potassium thiocyanate (7.6 g) and bromine (3.6 g) in acetic acid (60 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 (5 cc) in ethanol (30 cc) and recrystallized in absolute ethanol (50 cc). N-Ethyl-2-(2-imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanesulphonamide hydrochloride (3.0 g), m.p. 240° C., is thereby obtained.

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-84975bf25bc841d7898d13d160c29b5f
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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