Methanesulfonyl chloride → N-(3-amino-5-trifluoromethyl-phenyl)-methanesulfonamide

HRID 423863Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH2:10])[CH:6]=[C:7]([NH2:9])[CH:8]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1.C(Cl)Cl>[NH2:9][C:7]1[CH:6]=[C:5]([NH:10][S:14]([CH3:13])(=[O:16])=[O:15])[CH:4]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:8]=1

Participants

Conditions

Temperature: 8 °C

Procedure

A solution of 5-trifluoromethyl-benzene-1,3-diamine (250 mg, 1.42 mmol) in pyridine (0.52 mL) and CH2Cl2 (6.5 mL) was cooled to 0° C. Methanesulfonyl chloride (171 mg, 1.49 mmol) was slowly added at such a rate that the temperature of the solution remained below 10° C. The mixture was stirred at ˜8° C. and then allowed to warm to room temperature after 30 min. After stirring at room temperature for 4 h, reaction was almost complete as indicated by LCMS analysis. The reaction mixture was quenched with sat. aq. NH4Cl (10 mL) solution, extracted with CH2Cl2 (4×10 mL), dried over Na2SO4, filtered, and concentrated to yield N-(3-amino-5-trifluoromethyl-phenyl)-methanesulfonamide (D-19) as a reddish semisolid (0.35 g, 97%), which was used without further purification. 1H-NMR (CDCl3, 300 MHz) δ 6.76 (m, 1H), 6.70 (m, 1H), 6.66 (s, 1H), 3.02 (s, 3H); ESI-MS 255.3 m/z (MH+).

Workup

customremained below 10° C
temperatureto warm to room temperature after 30 min
stirringAfter stirring at room temperature for 4 h
customreaction
customThe reaction mixture was quenched with sat. aq. NH4Cl (10 mL) solution
extractionextracted with CH2Cl2 (4×10 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0f95de4514df45729e32cd23a526d95f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101767B2

Reaction notes

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