Water → N-(dibenzo[b,d]furan-2-ylmethyl)-2-methylpropane-2-sulfinamide

HRID 594382Notes

Reaction equation

HRID 594382 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[N:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17].[BH4-].[Na+].O>CO.C(Cl)Cl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86695630N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

Product 1

HCID 86695631N-(dibenzo[b,d]furan-2-ylmethyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide (2.260 g; 7.55 mmol) in anh. MeOH (27 ml) and anh. DCM (57 ml) was treated with NaBH4 (343 mg; 9.06 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 10 min. Water and DCM were added, and the organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording N-(dibenzo[b,d]furan-2-ylmethyl)-2-methylpropane-2-sulfinamide as a yellow solid. LC-MS (conditions A): tR=0.82 min.; [M+H]+: 302.01 g/mol.

Workup

  1. dry with materialthe organic layer was then dried over anh. MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-81c5c27ce73f482586f0cb35f3591fcb
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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