Dimethylformamide → 4-(2-Chloro-5-fluoro-benzoylamino)-3-methoxy-benzoyl chloride

HRID 2246068Notes

Reaction equation

HRID 2246068 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:31])=O>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([Cl:31])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 592180674-(2-Chloro-5-fluoro-benzoylamino)-3-methoxy-benzoic acid

Product 1

HCID 114619844-(2-Chloro-5-fluoro-benzoylamino)-3-methoxy-benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35 (152 g, 0.45 mol, 1 equiv.) was suspended in dichloromethane (1.5 L) and dimethylformamide (1 mL) was added. Oxalyl chloride (71.6 g, 0.56 mol, 1.2 equiv.) was added drop-wise over 30 minutes at 0° C. After addition, the cold bath was removed and the reaction mixture was further stirred at room temperature for 3.5 h. The solvent and any unreacted oxalyl chloride were evaporated to yield a white solid, which was further dried on a rotary evaporator under vacuum at 40° C. overnight to yield dry 4-(2-chloro-5-fluoro-benzoylamino)-3-methoxy-benzoyl chloride 36 as a white solid. 1H NMR (400 MHz, CDCl3) δ: 8.97 (s, 1H), 8.71 (d, 1H), 7.91 (dd, 1H), 7.60 (d, 1H), 7.57 (dd, 1H), 7.47 (dd, 1H), 7.21-7.15 (m, 1H), 3.99 (s, 3H). MS (ES) m/z 339.9 (MH)+.

Workup

  1. additionAfter addition
  2. customthe cold bath was removed
  3. customThe solvent and any unreacted oxalyl chloride were evaporated
  4. customto yield a white solid, which
  5. customwas further dried on a rotary evaporator under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-89ed6ca93b1948fcafc950ebf05ed006
Source dataset
uspto-grants-2010_03
Patent number
US07687494B2

Reaction notes

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