Sulfuric Acid → HCID 12081709, compound

HRID 498161Notes

Reaction equation

HRID 498161 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:27]=[CH:26][C:10]([O:11][C:12]2[CH:13]=[C:14]([C:22]([O:24][CH3:25])=[O:23])[CH:15]=[C:16]([CH:21]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:9][CH:8]=1.N([O-])=[O:29].[Na+]>O>[OH:29][C:7]1[CH:27]=[CH:26][C:10]([O:11][C:12]2[CH:13]=[C:14]([C:22]([O:24][CH3:25])=[O:23])[CH:15]=[C:16]([CH:21]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12080911HCID 12080911, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12081709HCID 12081709, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Into a 1 liter four-necked flask equipped with a thermometer, a stirrer and a dropping funnel, 450 ml of ion-exchanged water, 75 ml of a concentrated sulfuric acid and 45.20 g (0.15 moles) of dimethyl 5-(4-aminophenoxy)isophthalate obtained in accordance with the same procedures as those conducted in Example 5 were placed and the resultant mixture was stirred. The flask was cooled at a temperature of 50° C. or lower. Into the cooled flask, a solution prepared by dissolving 12.42 g (0.18 moles) of sodium nitrite into 25 ml of distilled water was added dropwise over 20 minutes. The resultant mixture was stirred at a temperature of 5° C. or lower for 40 minutes and at 100° C. for 2 hours. The formed precipitates were separated by filtration and, after a treatment with active carbon in methanol, recrystallized from methanol. The formed solid substance was separated by filtration and dried at 50° C. for 1 day under a reduced pressure and 23.58 g of a product was obtained (the yield: 52%).

Workup

  1. customobtained in accordance with the same procedures as
  2. customInto the cooled flask, a solution prepared
  3. additionwas added dropwise over 20 minutes
  4. customThe formed precipitates
  5. customwere separated by filtration
  6. customafter a treatment with active carbon in methanol, recrystallized from methanol
  7. customThe formed solid substance was separated by filtration
  8. customdried at 50° C. for 1 day under a reduced pressure

Sources & evidence

ORD record
ord-03a2c29fabc14eea9c69b3045a4600af
Source dataset
uspto-grants-2005_09
Patent number
US06949674B2

Reaction notes

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