Pyridine → HCID 59317126, compound

HRID 2410251Notes

Reaction equation

HRID 2410251 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH2:15]([O:22][C:23]1[CH:31]=[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:29]([Br:40])=[CH:28][C:24]=1[C:25](Cl)=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:15]([O:22][C:23]1[CH:31]=[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:29]([Br:40])=[CH:28][C:24]=1[C:25]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])=[O:26])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7242O-ToluidineHCID 77174849HCID 77174849, compound

Product 1

HCID 59317126HCID 59317126, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2.8 l of o-toluidine and 2.5 l of pyridine are added to 50 l of dichloromethane at 3° C. 13.6 kg of 2,4-bisbenzyloxy-5-bromobenzoyl chloride (toluene-moist) suspended in 35 l of dichloromethane are added to this solution over the course of 2 h. The mixture is subsequently stirred overnight at 23° C., and the solid is filtered off and rinsed with dichloromethane (2× with 5 l each time). The crude product obtained in this way (8 kg) is dissolved in 40 l of dichloromethane and extracted successively with 40 l of distilled water, 50 l of hydrochloric acid (˜1 mol/l; prepared from 5 l of HCl w: 37% and 50 l of water). The organic phase is subsequently washed with 50 l of water. The organic phase is dried for 3 days using 6 kg of sodium sulfate. The drying agent is filtered off with suction via a suction filter, and the filtrate is evaporated to dryness in a rotary evaporator. Recrystallisation from ethanol (35 l, 65° C.) and drying (50° C./35 mbar) to constant weight gives 10.84 kg (82%) of 2,4-bisbenzyloxy-5-bromo-N-o-tolylbenzamide (m.p. 174.5° C.-176° C.; MW 502.4).

Workup

  1. additionare added to this solution over the course of 2 h
  2. filtrationthe solid is filtered off
  3. washrinsed with dichloromethane (2× with 5 l each time)
  4. customThe crude product obtained in this way (8 kg)
  5. extractionextracted successively with 40 l of distilled water, 50 l of hydrochloric acid (˜1 mol/l; prepared from 5 l of HCl w: 37% and 50 l of water)
  6. washThe organic phase is subsequently washed with 50 l of water
  7. customThe organic phase is dried for 3 days
  8. filtrationThe drying agent is filtered off with suction via a suction
  9. filtrationfilter
  10. customthe filtrate is evaporated to dryness in a rotary evaporator
  11. customRecrystallisation from ethanol (35 l, 65° C.)
  12. customdrying (50° C./35 mbar) to constant weight

Sources & evidence

ORD record
ord-7fb0c0e936d441ab8715e7d47664ea24
Source dataset
uspto-grants-2014_08
Patent number
US08816070B2

Reaction notes

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