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

HRID 517219Notes

Reaction equation

HRID 517219 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[CH3:22])=O.[C:23]1([S:29]([O-:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+]>O1CCCC1.O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([N:5]([CH2:1][S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[C:4](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[C:15]([CH3:22])[CH:16]=1)#[N:19]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 109096954-Formyl-3-methylbenzonitrile

Product 1

HCID 86732338tert-Butyl (4-Cyano-2-methylphenyl)(phenylsulfonyl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Formic acid (3.3 mL, 88 mmol) is added to a mixture of tert-butyl carbamate (1.61 g, 13.8 mmol), 4-formyl-3-methylbenzonitrile (2.00 g, 13.8 mmoo) and sodium benzenesulfinate (2.26 g, 13.8 mmol) in a mixture of tetrahydrofuran (7 mL) and water (18 mL), and the mixture is stirred at room temperature for 4 days. The tetrahydrofuran is removed under reduced pressure. The precipitate is filtered and dried. Yield: 3.77 g.

Workup

  1. customThe tetrahydrofuran is removed under reduced pressure
  2. filtrationThe precipitate is filtered
  3. customdried

Sources & evidence

ORD record
ord-c0b60ae43a3e4b7aa485dc98923b4393
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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