Hydrochloric Acid → 3-chloro-2-methyl-N-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamide

HRID 1245631Notes

Reaction equation

HRID 1245631 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:12])[S:5][C:6]=1[CH2:7][C:8]([Cl:11])([Cl:10])[Cl:9].[Cl:13][C:14]1[C:15]([CH3:24])=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.Cl>O>[Cl:13][C:14]1[C:15]([CH3:24])=[C:16]([S:20]([NH:12][C:4]2[S:5][C:6]([CH2:7][C:8]([Cl:11])([Cl:9])[Cl:10])=[C:2]([CH3:1])[N:3]=2)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 156488254-Methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-ylamine

Product 1

HCID 111547603-chloro-2-methyl-N-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared similar to EXAMPLE 6 according to METHOD A from 4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-ylamine (123 mg, 0.5 mmol) and 3-chloro-2-methylbenzenesulfonyl chloride (112.5 mg, 0.5 mmol). The solution was allowed to stand at r.t. overnight. Water (5 mL) was added and the resulted solution was made acidic with conc. HCl. The precipitate was filtered, washed with water and dried. Flash column chromatography of the precipitate on silica gel, eluted with a mixed solvents of ethyl ether and hexane (2:1) gave the title compound as a solid (165 mg, 76% yield). The product can be recrystallized from ethyl acetate and hexane: MS m/e: 439, 437, 435, 433.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. washFlash column chromatography of the precipitate on silica gel, eluted with a mixed solvents of ethyl ether and hexane (2:1)

Sources & evidence

ORD record
ord-25ad22687a594644be217657c9a94091
Source dataset
uspto-grants-2006_10
Patent number
US07125900B2

Reaction notes

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