Dichloromethane → HCID 66603388, compound

HRID 1797889Notes

Reaction equation

HRID 1797889 reaction equation
ClCCl.[O:4]=[C:5]1[N:9]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[NH:6]1.C(Cl)(=O)C([Cl:23])=O>CN(C)C=O>[O:4]=[C:5]1[N:9]([CH2:10][CH2:11][CH2:12][C:13]([O:15][Cl:23])=[O:14])[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[NH:6]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 132517844-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acid

Product 1

HCID 66603388HCID 66603388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Dichloromethane (3772 L) and then 4-(2-oxo-2,3-dihydrobenzimidazol-1-yl)butyric acid (525 kg; 2.4 kmol) were charged to a stirred-tank reactor, followed by N,N-dimethylformamide (21 L). The resulting mixture was cooled to 10° C. Afterward, oxalyl chloride (326.8 kg)) was dosed at 10-15° C. over 2-3 hours while stirring. The resulting mixture was then stirred at 15-20° C. for an additional 1-3 hours. All the above steps were conducted under a N2 atmosphere. Conversion was checked by in-process control (“IPC”).

Workup

  1. stirringThe resulting mixture was then stirred at 15-20° C. for an additional 1-3 hours

Sources & evidence

ORD record
ord-82eac5a66cfe4c2ab0baa0d0f5b854bc
Source dataset
uspto-grants-2013_01
Patent number
US08343956B2

Reaction notes

Loading…