Triethylamine → HCID 20137301, compound

HRID 1253182Notes

Reaction equation

HRID 1253182 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[N:5]=[C:4]([CH3:13])[N:3]=1.C(N(CC)CC)C.[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][NH2:26])[CH3:22]>C1C=CC=CC=1>[ClH:1].[ClH:1].[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][NH:26][C:2]1[C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[N:5]=[C:4]([CH3:13])[N:3]=1)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60993N,N-DiethylethylenediamineHCID 608089HCID 608089, compound

Product 1

HCID 20137301HCID 20137301, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture containing 2 g of 4-chloro-2-methyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one, 1.52 g of triethylamine 1.16 g of 2-diethylaminoethylamine and 50 ml of abs. benzene is refluxed while stirring for 20 hours, then evaporated. After adding water to the residue, the pH is adjusted to 3 and the mixture is extracted with chloroform. The aqueous phase is alkalized to pH 9, extracted with chloroform, the latter organic phase is washed with water, dried and evaporated. The oily residue is taken up in ethanol and ethanolic hydrogen chloride solution is added. The precipitate is filtered to give 0.56 g (16%) of the product, m.p.: 252°-255° C.

Workup

  1. customevaporated
  2. additionAfter adding water to the residue
  3. extractionthe mixture is extracted with chloroform
  4. extractionextracted with chloroform
  5. washthe latter organic phase is washed with water
  6. customdried
  7. customevaporated
  8. additionethanolic hydrogen chloride solution is added
  9. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-5111eb8ee3474911b63ac5ff8b1e9789
Source dataset
uspto-grants-1988_05
Patent number
US04748175

Reaction notes

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