Benzocaine → HCID 54337669, compound

HRID 845505Notes

Reaction equation

HRID 845505 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[CH:18][CH:19]=[CH:20][C:21](O)=[O:22])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:30][C:31]1[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][CH:32]=1>C(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[C:35]([C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:21](=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)=[CH:41][CH:40]=1)([O:37][CH2:38][CH3:39])=[O:36]

Participants

7

Reactant 3

HCID 2337BenzocaineHCID 65578Oxalyl chlorideHCID 54210808HCID 54210808, compound

Product 1

HCID 54337669HCID 54337669, compoundYield 20.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-(1-benzylindol-3-yl)-2,4-pentadienoic acid (0.9 g, 2.9 mmol) in 20 ml of methylene chloride was added dropwise with stirring at room temperature 0.26 ml (0.38 g, 3 mmol) of oxalyl chloride, followed by four drops of N,N-dimethyl-formamide (DMF). The reaction mixture was stirred for an additional 90 min. and concentrated on rotary evaporator. The residue was dissolved in 10 ml of anhydrous methylene chloride and added dropwise to a solution of ethyl p-aminobenzoate (0.44 g, 2.7 mmol) in 5 ml of methylene chloride and 1.3 ml of pyridine. The resulting mixture was stirred at room temperature for 18 hours and washed with saturated aqueous sodium bicarbonate solution and water, dried (MgSO4) and mixture. Purification by a dry column (hexane:ethyl acetate, 2:1) followed by crystallization (acetone-petroleum ether) afforded 250 mg of yellow crystals, m.p. 162-166. MS(EI)=450(M+), 286 (M+--HNC6H4CO2C2H5 ); nmr (CDCl3): δ1.35 (t, J=7 Hz, 3), δ4.28(q, J=7 Hz, 2), δ5.22(s, 2), δ5.95(d, J=15 Hz, 1).

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated on rotary evaporator
  3. dissolutionThe residue was dissolved in 10 ml of anhydrous methylene chloride
  4. stirringThe resulting mixture was stirred at room temperature for 18 hours
  5. washwashed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried (MgSO4) and mixture
  7. customPurification by a dry column (hexane:ethyl acetate, 2:1)
  8. customfollowed by crystallization (acetone-petroleum ether)

Sources & evidence

ORD record
ord-97229b75740d425197b8bfbee8309b76
Source dataset
uspto-grants-1988_07
Patent number
US04758586

Reaction notes

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