Formic Acid → HCID 59536928, compound

HRID 709130Notes

Reaction equation

HRID 709130 reaction equation
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].[Na+].[C:10]1([S:16]([O-:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:19][C:20]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C(O)=O>CO.O>[Cl:19][C:20]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 357452,3-DichlorobenzaldehydeHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 59536928HCID 59536928, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

At RT, 2.23 g (19.0 mmol) of tert-butyl carbamate and 6.25 g (38.1 mmol) of benzenesulphinic acid sodium salt were initially charged in 55 ml of methanol/water (1:2), and 5.00 g (28.6 mmol) of 2,3-dichlorobenzaldehyd and then 1.43 ml (37.9 mmol) of formic acid were added. The reaction mixture was stirred at RT for 2 days. The precipitated solid was filtered off with suction and washed with water and twice with diethyl ether. From the ethereal filtrate, 3.47 g of 2,3-dichlorobenzaldehyde were recovered after removal of the solvent on a rotary evaporator. The solid which was filtered off with suction was dried under high vacuum. This gave 2.22 g (19% of theory) of the title compound.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with water and twice with diethyl ether
  3. customFrom the ethereal filtrate, 3.47 g of 2,3-dichlorobenzaldehyde were recovered
  4. customafter removal of the solvent
  5. customon a rotary evaporator
  6. filtrationThe solid which was filtered off with suction
  7. customwas dried under high vacuum

Sources & evidence

ORD record
ord-07d0a62548844ec88049e02d1020db50
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

Loading…