Dimethylformamide → HCID 22767733, compound

HRID 1111739Notes

Reaction equation

HRID 1111739 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[C:6]1([NH2:24])[N:7]=[C:8]([NH2:23])[N:9]=[C:10]2[C:22]=1[C:21]1[C:20]3C[CH2:18][CH2:17][CH2:16][C:15]=3NC=1[CH:12]=[CH:11]2.[H-].[Na+].CI>C(O)(=O)C>[CH3:1][N:2]1[C:5]2[CH:12]=[CH:11][C:10]3=[N:9][C:8]([NH2:23])=[N:7][C:6]([NH2:24])=[C:22]3[C:21]=2[C:20]2[CH2:15][CH2:16][CH2:17][CH2:18][C:3]1=2

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22767700HCID 22767700, compound

Product 1

HCID 22767733HCID 22767733, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dry dimethylformamide (150 ml.), 4.62 g. 8,9,10,11-tetrahydro-7H-pyrimido[4,5-c]carbazole-1,3-diamine and 0.96 g. ca. 50% sodium hydride-mineral oil dispersion are stirred, under nitrogen, for 1 hour. A solution of 2.84 g. methyl iodide in 10 ml. dry dimethylformamide is added during 10 minutes and stirring is continued for ca. 2 hours. Glacial acetic acid (20 ml.) is added and the solvent is removed. The residue is stirred with 12 g. sodium methoxide-150 ml. methanol for 2 hours and the mixture is diluted with 750 ml. water. The solids are collected, washed with water, dried, twice recrystallized from methanol and thoroughly dried to yield 1.96 g. title compound, m.p. 288°-292° (softens 285°).

Workup

  1. customthe solvent is removed
  2. stirringThe residue is stirred with 12 g
  3. waitmethanol for 2 hours
  4. additionthe mixture is diluted with 750 ml
  5. customThe solids are collected
  6. washwashed with water
  7. customdried
  8. customtwice recrystallized from methanol
  9. customthoroughly dried
  10. customto yield 1.96 g

Sources & evidence

ORD record
ord-a3ccdda6bdb743eab83641e8551534bd
Source dataset
uspto-grants-1978_10
Patent number
US04118561

Reaction notes

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