Water → HCID 13491959, compound

HRID 979071Notes

Reaction equation

HRID 979071 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([NH2:21])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)(O)[O-].[Na+].O.Cl[CH2:29][C:30](Cl)=[O:31].[CH3:33][C:34](CC(C)C)=[O:35]>>[O:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:33][C:34](=[O:35])[NH:21][C:16]=4[CH:15]=3)=[CH:3][C:2]=2[NH:1][C:30](=[O:31])[CH2:29]1

Participants

6

Reactant 5

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 7909Methyl Isobutyl KetoneHCID 516892Sodium BicarbonateHCID 20201605HCID 20201605, compound

Product 1

HCID 13491959HCID 13491959, compound

Procedure

To a suspension of 1.5 g of 1,5-bis(3-amino-4-hydroxyphenyl)pentane (0.0052 mol) in 7 ml of isobutyl methyl ketone was added 1.05 g (0.0125 mole) of sodium bicarbonate and 5 ml of water. The suspension was stirred in an ice bath and 1.4 g (0.0124 mole) of chloroacetyl chloride was added dropwise. After addition, the mixture was allowed to come to room temperature and then was refluxed for 4 hours. After cooling, the resulting crystalline solid was filtered and washed with acetone to yield 0.4 g of off-white product of m.p. 189°-190° C.

Workup

  1. additionAfter addition
  2. customto come to room temperature
  3. temperaturewas refluxed for 4 hours
  4. temperatureAfter cooling
  5. filtrationthe resulting crystalline solid was filtered
  6. washwashed with acetone

Sources & evidence

ORD record
ord-cd287415cced43679b782906beca5239
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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