Toluene → HCID 19862811, compound

HRID 1165263Notes

Reaction equation

HRID 1165263 reaction equation
C1(C)C=CC=CC=1.Cl[CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=1[NH2:21].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>O>[O:26]1[CH2:27][CH2:28][N:23]([CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[NH2:21])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8083MorpholineHCID 19862798HCID 19862798, compound

Product 1

HCID 19862811HCID 19862811, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 35 ml of toluene, 4.6 g of (3-chloropropyl)-2,4-diaminobenzoate and 3.5 g of morpholine was refluxed for 10 hrs, cooled to room temperature, and poured into 70 ml of water with stirring. The precipitate was filtered, washed with hexane and dried. Recrystallization from toluene gave 2.6 g (3-morpholinopropyl)-2,4-diaminobenzoate, a white solid, mp 96° C.

Workup

  1. temperaturewas refluxed for 10 hrs
  2. filtrationThe precipitate was filtered
  3. washwashed with hexane
  4. customdried
  5. customRecrystallization from toluene

Sources & evidence

ORD record
ord-d91c98b6083b42d28e154dc79ab3de41
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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