Dimethylformamide → HCID 13451689, compound

HRID 1248008Notes

Reaction equation

HRID 1248008 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][N:7]3[CH:15]=[CH:16][CH:17]=[C:6]3[C:5]=12.P(Cl)(Cl)(Cl)=O.CN(C)[CH:25]=[O:26]>>[N:1]1[CH:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][N:7]3[CH:15]=[C:16]([CH:25]=[O:26])[CH:17]=[C:6]3[C:5]=12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 13451688HCID 13451688, compound

Product 1

HCID 13451689HCID 13451689, compound

Procedure

9H-Imidazo[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine (8.00 g, 36.1 mmoles) was heated in dry dimethylformamide (120 mL) at 120° C. in the presence of phosphoryl chloride (10.4 g, 6.32 mL). After 2 hours, the reaction mixture was poured onto ice-water and then extracted several times with chloroform. The combined extracts were washed with water, brine, dried and evaporation of solvent gave a tan residual solid. Crystallization of the solid form toluene-hexane gave 9H-imidazo[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine-12-carboxaldehyde (3.57 g): mp 203°-205° C.; Anal. Calcd for C15H11N3O: C, 72.27% H, 4.45% N, 16.86%, Found: C, 72.08% H, 4.51% N, 16.77%.

Workup

  1. additionthe reaction mixture was poured onto ice-water
  2. extractionextracted several times with chloroform
  3. washThe combined extracts were washed with water, brine
  4. customdried
  5. customevaporation of solvent
  6. customgave a tan residual solid
  7. customCrystallization of the solid form toluene-hexane

Sources & evidence

ORD record
ord-6ba3d26280f74f2b820f07ac0383b622
Source dataset
uspto-grants-1985_06
Patent number
US04521534

Reaction notes

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