Nitrite → Valpromide

HRID 1704693Notes

Reaction equation

HRID 1704693 reaction equation
[CH2:1]([CH:4]([CH2:7][CH2:8][CH3:9])[C:5]#[N:6])[CH2:2][CH3:3].S(=O)(=O)(O)[OH:11].N([O-])=O.[Na+].N([O-])=O>>[CH2:1]([CH:4]([CH2:7][CH2:8][CH3:9])[C:5]([NH2:6])=[O:11])[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 946NitriteHCID 1118Sulfuric Acid2×HCID 833302-Propylvaleronitrile2×HCID 23668193Sodium Nitrite

Product 1

HCID 71113Valpromide

Procedure

As regards the hydrolysis of the di-n-propyl acetonitrile, this will advantageously be carried out by means of 80% by weight sulphuric acid in the proportion of 3 to 5 g of dilute acid/g of nitrile, for example, 3.75 g of dilute acid/g of nitrile over a period of 90 minutes at 80°-85° C. and adding to the resulting amide an aqueous solution of sodium nitrite in the proportion of 1.4 mol of nitrite/mol of di-n-propyl acetonitrile, the reaction taking place for 2 hours at 40°-50° C. It will also be just as advantageous to use a 75% by weight sulphuric acid aqueous solution in the proportion of 1.7 g of dilute acid/g of nitrile for 30 minutes at 140° C., to obtain the intermediate di-n-propyl acetamide, which is hydrolysed in the same sulphuric acid medium in the presence of sodium nitrite in the proportion of 1.4 to 1.5 mol of nitrite/mol of di-n-propyl acetonitrile for one hour at 50°-60° C.

Workup

  1. customfor 2 hours
  2. customat 40°-50° C
  3. customfor 30 minutes
  4. customat 140° C.

Sources & evidence

ORD record
ord-c5898a57f50a472bbcac5877e42c97cc
Source dataset
uspto-grants-1978_11
Patent number
US04127604

Reaction notes

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