Formaldehyde → HCID 13225530, compound

HRID 464531Notes

Reaction equation

HRID 464531 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([CH3:22])[N:19]=[CH:18][C:7]=3[CH2:8][NH:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[CH2:25]=O>C(O)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([CH3:22])[N:19]=[CH:18][C:7]=3[CH2:8][N:9]([CH3:25])[CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 13225526HCID 13225526, compound

Product 1

HCID 13225530HCID 13225530, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 4 g (11 mmole) of 9-chloro-7-(2-chlorophenyl)-6,7-dihydro-2-methyl-5H-pyrimido[5,4-d][2]benzazepine 2 ml of 88% formic acid and 2 ml of 37.5% formaldehyde solution was heated on the steambath for 3 hours. The reaction mixture was poured into an excess of dilute ice cold sodium hydroxide and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was crystallized from ether to give the crude product, m.p. 155°-156° C. Recrystallization from ether gave the pure product as colorless prisms, m.p. 156°-157° C.

Workup

  1. temperaturewas heated on the steambath for 3 hours
  2. additionThe reaction mixture was poured into an excess of dilute ice cold sodium hydroxide
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to dryness
  6. customThe residue was crystallized from ether
  7. customto give the crude product, m.p. 155°-156° C
  8. customRecrystallization from ether

Sources & evidence

ORD record
ord-251680f4b11e4832a1c56a8b3a5d2643
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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