Acetic Anhydride → N-(4,6-Dichloropyrimidin-2-yl)formamide

HRID 1730143Notes

Reaction equation

HRID 1730143 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[C:10](OC(=O)C)(=[O:12])C>C(O)=O>[CH:10]([NH:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 21499405N-(4,6-Dichloropyrimidin-2-yl)formamideYield 77%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A 250 ml. three necked flask was fitted with a mechanical stirrer, a thermometer, and a reflux condenser with drying tube. To the flask was charged 70 ml. of a 98% formic acid and 3.85 g (0.025 mole) of 2-amino-4,6-dichloropyrimidine as prepared in example 1. Acetic anhydride, 30 ml. was added slowly with stirring to maintain temperature below 50° C. When the addition of acetic anhydride was complete, the mixture was heated for 6 more hours at 50° C and then allowed to stand overnight at room temperature. Excess formic acid and acetic anhydride were evaporated under vacuum. The solid residue was crystallized from 15 ml. of ethyl alcohol. There was obtained 3.7 g of 2-formamido-4,6-dichloropyrimidine (PY-24) in the form of white crystals, melting point, 142°-144° C, yield 77%.

Workup

  1. customthree necked flask was fitted with a mechanical stirrer
  2. customa thermometer, and a reflux condenser with drying tube
  3. additionTo the flask was charged 70 ml
  4. additionwas added slowly
  5. temperatureto maintain temperature below 50° C
  6. customExcess formic acid and acetic anhydride were evaporated under vacuum
  7. customThe solid residue was crystallized from 15 ml

Sources & evidence

ORD record
ord-38f04e15867449d794363b319ec721e0
Source dataset
uspto-grants-1976_11
Patent number
US03991190

Reaction notes

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