Formic Acid → 1,1-Dimethylethyl N-[(phenylsulfonyl)-3-pyridinylmethyl]carbamate

HRID 658143Notes

Reaction equation

HRID 658143 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9](=[O:16])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[NH2:10].[C:17]1([S:23]([O-:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].C(O)=O>O.CO>[C:17]1([S:23]([CH:7]([NH:10][C:9](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 103713-PyridinecarboxaldehydeHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 574352341,1-Dimethylethyl N-[(phenylsulfonyl)-3-pyridinylmethyl]carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Pyridine-3-carbaldehyde (5.36 g, 50 mmol), tert-butyl carbamate (11.7 g, 100 mmol, 2 equivalents), sodiumphenylsulfinate (20.36 g, 124 mmol, 2.48 equivalents), formic acid (1.89 ml, 2.30 g, 1 equivalent), methanol (55 ml) and water (111 ml) are mixed and vigorously stirred at room temperature for 3 d. The product precipitates in the form of colorless crystals which are collected by filtration, washed with water and a little MTBE and dried in vacuo. Yield: 4.10 g (24% of theory).

Workup

  1. customThe product precipitates in the form of colorless crystals which
  2. filtrationare collected by filtration
  3. washwashed with water
  4. dry with materiala little MTBE and dried in vacuo

Sources & evidence

ORD record
ord-11b4b1116ee34b45bf3e7fcf5e2e9cfb
Source dataset
uspto-grants-2011_12
Patent number
US08076285B2

Reaction notes

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