3-Chloro-1,2-propanediol → HCID 23500034, compound

HRID 980419Notes

Reaction equation

HRID 980419 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][CH2:19][CH:20]([OH:23])[CH2:21][OH:22]

Participants

5

Reactant 3

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

Product 1

HCID 23500034HCID 23500034, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 first heated on a boiling waterbath, while stirring. 0.216 mol (24 g) of 1-chloropropane-2,3-diol is added. The reaction mixture is heated on a boiling waterbath for 24 hours, 0.035 mol (3.5 g) of calcium carbonate and 0.066 mol (7.3 g) of 1-chloropropane-2,3-diol being simultaneously added seven times at intervals of three hours. The reaction mixture is filtered hot and the filtrate is diluted with 60 ml of water. After the filtrate has been cooled at 0° C. for 24 hours, the expected product, which has crystallised, is filtered off with suction. The product is washed with water and recrystallised three times from ethanol. It has a melting point of 150° C.

Workup

  1. temperatureare first heated on a boiling waterbath
  2. temperatureThe reaction mixture is heated on a boiling waterbath for 24 hours
  3. filtrationThe reaction mixture is filtered hot
  4. additionthe filtrate is diluted with 60 ml of water
  5. customthe expected product, which has crystallised
  6. filtrationis filtered off with suction
  7. washThe product is washed with water
  8. customrecrystallised three times from ethanol

Sources & evidence

ORD record
ord-bdcf6117b83347ac9233ab0c39a6a41f
Source dataset
uspto-grants-1987_01
Patent number
US04637821

Reaction notes

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