Formic Acid → tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate

HRID 517225Notes

Reaction equation

HRID 517225 reaction equation
[CH:1](O)=O.[C:4](=[O:11])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:5].C([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[S:22]([CH3:25])(=[O:24])=[O:23])=O.[C:26]1([S:32]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+]>O1CCCC1.O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([N:5]([CH2:1][S:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:34])=[O:33])[C:4](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[C:15]([S:22]([CH3:25])(=[O:23])=[O:24])[CH:16]=1)#[N:19]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 581337504-Formyl-3-(methylsulfonyl)benzonitrile

Product 1

HCID 86732345tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Formic acid (4.1 mL, 109 mmol) is added to a mixture of tert-butyl carbamate (2.00 g, 17.1 mmol), 4-formyl-3-(methylsulfonyl)benzonitrile (3.57 g, 17.1 mmol) and sodium benzenesulfinate (2.80 g, 17.1 mmol) in a mixture of tetrahydrofuran (12 mL) and water (48 mL), and the mixture is stirred at room temperature for 5 days. Water (60 mL) is added, and the precipitated is filtered, washed with water and dried. Yield: 5.00 g.

Workup

  1. filtrationthe precipitated is filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-75a30bb2f3244af19139c882d93ef552
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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