Chloroacetonitrile → HCID 86742194, compound

HRID 1253186Notes

Reaction equation

HRID 1253186 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH3:5][C:6]1[N:7]=[C:8]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:9]2[O:10][CH:11]([NH2:17])[C:12](=[O:16])[NH:13][C:14]=2[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:3]([CH2:2][N:13]1[C:12](=[O:16])[CH:11]([NH2:17])[O:10][C:9]2[C:8]([CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:7][C:6]([CH3:5])=[N:15][C:14]1=2)#[N:4]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 70415936HCID 70415936, compound

Product 1

HCID 86742194HCID 86742194, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

0.25 g of chloroacetonitrile dissolved in 50 ml of methyl ethyl ketone is dropped within 15 minutes to a suspension containing 0.88 g of 2-methyl-4-[2-(4-morpholinyl)-ethyl]-amino-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one base (e.g. prepared as described in Example 23) and 0.5 g of anhydrous potassium carbonate in 15 ml of methyl ethyl ketone under boiling and stirring. The mixture is further boiled under stirring for 8 hours, the precipitate is filtered as hot and washed with methyl ethyl ketone. The filtrate is evaporated and the residue is triturated with diisopropyl ether. After filtering, the solid is washed with diisopropyl ether and dried to give 0.91 g (91%) of the product, m.p.: 126°-128° C.

Workup

  1. additionis dropped within 15 minutes to a suspension
  2. stirringunder stirring for 8 hours
  3. filtrationthe precipitate is filtered as hot and
  4. washwashed with methyl ethyl ketone
  5. customThe filtrate is evaporated
  6. customthe residue is triturated with diisopropyl ether
  7. filtrationAfter filtering
  8. washthe solid is washed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-33bf2bd77ea64cfe89be6d62cc7eb6b2
Source dataset
uspto-grants-1988_05
Patent number
US04748175

Reaction notes

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