Sodium Sulfate → HCID 66756625, compound

HRID 472487Notes

Reaction equation

[BH4-].[Li+].C([O:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH3:14])C.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.ClCCl>[OH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([CH3:14])[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

Conditions

Temperature: 5 °C

Procedure

195 c) To a cooled, stirred suspension of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (0.630 mL, 1.26 mmol) at 5° C. was added dropwise a solution of 2-(methanesulfonyl-methyl-amino)-benzoic acid ethyl ester (1.08 g, 4.20 mmol) in tetrahydrofuran (10 mL). Gas evolution was noted. The mixture was stirred for 10 minutes at 5° C. then at room temperature for 3 hours. The mixture was cooled to 5° C. and saturated aqueous ammonium chloride (5 mL) was added dropwise. Vigorous gas evolution was noted. The mixture was stirred for 15 minutes then warmed to room temperature for 30 minutes. Sodium sulfate was added to granulate aluminium salts. The mixture was diluted with dichloromethane (50 mL), filtered through a plug of diatomaceous earth and evaporated. N-(2-Hydroxymethyl-phenyl)-N-methyl-methanesulfonamide was isolated as a yellow oil (0.931 g, 100%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.61 (d, J=7.3 Hz, 1H), 7.44-7.35 (m, 2H), 7.28-7.24 (m, 1H), 4.74 (br s, 2H), 3.29 (s, 3H), 2.98 (s, 3H), 2.90-2.81 (m, 1H). MS=238 (M+Na)+.

Workup

stirringThe mixture was stirred for 10 minutes at 5° C.
stirringThe mixture was stirred for 15 minutes
temperaturethen warmed to room temperature for 30 minutes
filtrationfiltered through a plug of diatomaceous earth
customevaporated

Sources & evidence

ORD record: ord-ff42120881a646eb8cd3260f3c0e9da1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

Loading…