3-Chloro-1,2-propanediol → HCID 20446520, compound

HRID 2417752Notes

Reaction equation

HRID 2417752 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[Ca+2].Cl[CH2:19][CH:20]([OH:23])[CH2:21][OH:22]>O>[CH3:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH:4][CH:21]([OH:22])[CH:20]([OH:23])[CH3:19]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediol2×HCID 10112Calcium Carbonate2×HCID 54879441,4-Benzenediamine, 2-methyl-5-nitro-

Product 1

HCID 20446520HCID 20446520, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

0.2 mol (33.4 g) of 2-methyl-4-amino-5-nitroaniline and 0.1 mol (10 g) of calcium carbonate, suspended in 100 ml of water, are heated beforehand on a boiling water-bath, whilst stirring. 0.216 mol (24 g) of 1-chloropropane-2,3-diol is added. The reaction mixture is heated for 24 hours on the boiling water-bath, seven portions each containing 0.035 mol (3.5 g) of calcium carbonate and 0.066 mol (7.3 g) of 1-chloropropane-2,3-diol being added, one every three hours. The hot reaction mixture is filtered and the filtrate is diluted with 60 ml of water. After cooling for 24 hours at 0° C., the expected product, which has crystallised, is filtered off. The product is washed with water and recrystallised three times from ethanol. It melts at 150° C.

Workup

  1. temperatureare heated beforehand on a boiling water-bath
  2. additionadded
  3. customevery three hours
  4. filtrationThe hot reaction mixture is filtered
  5. additionthe filtrate is diluted with 60 ml of water
  6. customthe expected product, which has crystallised
  7. filtrationis filtered off
  8. washThe product is washed with water
  9. customrecrystallised three times from ethanol

Sources & evidence

ORD record
ord-894fd08b64e544e8bdc869a4f8a43b47
Source dataset
uspto-grants-1984_09
Patent number
US04470826

Reaction notes

Loading…