Acetic Acid → HCID 10824292, compound

HRID 1369380Notes

Reaction equation

HRID 1369380 reaction equation
[CH3:1][NH2:2].C(O)(=O)C.Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([Cl:17])[N:11]=[C:10]([NH:18][C:19](=[O:21])[CH3:20])[N:9]=1.O>O1CCCC1>[Cl:17][C:12]1[C:13]([N+:14]([O-:16])=[O:15])=[C:8]([NH:2][CH3:1])[N:9]=[C:10]([NH:18][C:19](=[O:21])[CH3:20])[N:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6329MethylamineHCID 301038N-(4,6-Dichloro-5-nitropyrimidin-2-yl)ethanimidic acid

Product 1

HCID 10824292HCID 10824292, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution (reagent A) of 2 liters of a 40% aqueous solution of methylamine and 1.5 liters of acetic acid previously prepared at not higher than 10° C. was weighed and taken out in an amount of 1.8 liters and added dropwise into a solution of 1.5 kg of N1-(4,6-dichloro-5-nitro-2-pyrimidinyl)acetamide in 15 liters of tetrahydrofuran with stirring under ice-cooling over 1 hour. The addition was carried out keeping the bulk temperature at 4° C. or lower. After the mixture was stirred for 30 minutes under ice-cooling, 450 ml of the reagent A was further added. After further 30 minutes, 450 ml of the reagent A was added again followed by stirring for 40 minutes. Ice (4.5 kg) was added to the reaction mixture followed by adding 10 liters of cold water. The resulting crystals were collected by filtration and washed with 1 liter of water twice and with 1 liter of ether twice. Then it was dried at 50° C. for 6 hours to give 1253 g of N1-(4-Chloro-6-methylamino-5-nitro-2-pyrimidinyl)acetamide. The yield was 85%.

Workup

  1. temperaturecooling over 1 hour
  2. additionThe addition
  3. customat 4° C.
  4. stirringAfter the mixture was stirred for 30 minutes under ice-
  5. temperaturecooling
  6. stirringby stirring for 40 minutes
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with 1 liter of water twice
  9. customThen it was dried at 50° C. for 6 hours

Sources & evidence

ORD record
ord-e6be86aee79f464ba16cfbb370870724
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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