Sulfuric Acid → HCID 86736818, compound

HRID 1448982Notes

Reaction equation

HRID 1448982 reaction equation
[NH2:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13](=[O:17])[CH2:14][C:15]#[N:16])=[O:11])=[O:3].O1CCOCC1.[N:24]([O-])=[O:25].[Na+].S(=O)(=O)(O)O>O.C(OCC)(=O)C.C(O)(=O)C>[NH2:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13](=[O:17])[C:14]([C:15]#[N:16])=[N:24][OH:25])=[O:11])=[O:3]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 20374839HCID 20374839, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86736818HCID 86736818, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 72 g of 1-(5-aminocarbonyl-pentyl)-3-(2-cyanoacetyl)-urea, 125 ml of water, 125 ml of dioxane, 23.2 g of sodium nitrite and 1 ml of acetic acid was adjusted to pH 4.5 to 5 at 50° C. by slowly adding 15% strength sulphuric acid dropwise. The reaction mixture was stirred at 50° C. for 2 hours, diluted with 600 ml of water and 600 ml of ethyl acetate, then cooled at 20° C. and adjusted to a pH value of 2. The crystals were separated off, washed with water and dried in vacuo. 61.3 g of 1-(5-aminocarbonyl-pentyl)-3-(2-cyano-2-oximinoacetyl)-urea of melting point 187°-189° C. were obtained.

Workup

  1. customwas adjusted to pH 4.5 to 5 at 50° C.
  2. temperaturecooled at 20° C.
  3. customThe crystals were separated off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-825aaca5f63740e08d0797510f14083a
Source dataset
uspto-grants-1980_02
Patent number
US04188401

Reaction notes

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