Ethyl Bromide → HCID 13659897, compound

HRID 1058532Notes

Reaction equation

HRID 1058532 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([N:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.N12CCCN=C1CCC[CH2:27][CH2:26]2.C(Br)C>C1C=CC=CC=1>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([N:7]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:26][CH3:27])=[O:13])=[CH:15][CH:16]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18668223HCID 18668223, compound

Product 1

HCID 13659897HCID 13659897, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-(Di-p-tolylamino)benzoic acid (69.7 g, 0.22 mol) dissolved in benzene (500 mL), was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (38 mL, 0.25 mol), followed by the addition of ethyl bromide (33 mL, 0.44 mol). The reaction was filtered to remove salts, washed with saturated ammonium chloride until neutral (1.5 L), washed with water, washed with brine, and dried over magnesium sulfate. The solvent was removed at 40° C. and the residual crystalline solid was washed with cold ethanol to give ethyl 4-(di-p-tolylamino)benzoate (57.4 g, 76% yield).

Workup

  1. filtrationThe reaction was filtered
  2. customto remove salts
  3. washwashed with saturated ammonium chloride until neutral (1.5 L)
  4. washwashed with water
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed at 40° C.
  8. washthe residual crystalline solid was washed with cold ethanol

Sources & evidence

ORD record
ord-aa807fc0c2144be49d59c3f6494df2cd
Source dataset
uspto-grants-2003_02
Patent number
US06517984B1

Reaction notes

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