Ethyl 4-amino-3-(chloromethyl)benzoate hydrochloride → HCID 178469028, compound

HRID 1586486Notes

Reaction equation

HRID 1586486 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[NH2:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]=1[CH2:26]Cl>C(O)(C)C>[NH2:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]=1[CH2:26][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 22394040Ethyl 4-amino-3-(chloromethyl)benzoate hydrochlorideHCID 178488032HCID 178488032, compound

Product 1

HCID 178469028HCID 178469028, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 1.30 g of 2-mercapto-5-methoxybenzimidazole instead of 2-mercaptobenzimidazole and 1.80 g of ethyl 4-amino-3-(chloromethyl)benzoate hydrochloride (prepared as for Example 70) instead of 2-(chloromethyl)-N,N-dimethylaniline in isopropyl alcohol. The basic extraction used 10% sodium hydroxide instead of sodium carbonate and 1,2-dichloroethane instead of dichloromethane. The 1,2-dichloroethane extract was dried over sodium sulfate, filtered, and concentrated in vacuo to a gum. Recrystallization from diethyl ether-hexane gave 650 mg of the title compound: m.p. 140-146° C. Anal. Calc'd. for C18H19N3O3S: C, 60.49; H, 5.36; N, 11.76; S, 8.90. Found: C, 60.27; H, 5.44; N, 11.39; S, 8.70.

Workup

  1. extractionThe basic extraction
  2. extractionThe 1,2-dichloroethane extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a gum
  6. customRecrystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-fb7211c70f824bf192ee27367143421d
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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