Ammonium Chloride → HCID 178495876, compound

HRID 1248007Notes

Reaction equation

HRID 1248007 reaction equation
[NH2:1][C:2]1[C:8]2=[CH:9][CH:10]=[CH:11][N:7]2[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=1.[Cl-].[NH4+].[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21]N>C1(C)C=CC=CC=1>[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21][NH:1][C:2]1[C:8]2=[CH:9][CH:10]=[CH:11][N:7]2[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 12595986HCID 12595986, compound

Product 1

HCID 178495876HCID 178495876, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11-Amino-5H-pyrrolo[2,1-c][1,4]benzodiazepine (described by W. B. Wright et al., J. Med. Chem., 23,462 (1980), 2.00 g, 10.1 mmol) and ammonium chloride (200 mg, 19 mmol) were stirred in dry toluene (50 mL) in the presence of aminoacetaldehyde dimethylacetal (8.8 mL) under refluxing conditions for 3 hr. The precipitate which formed in the beginning redissolved to afford a brown solution. The reaction mixture was cooled in ice-water, washed with 10% (v/v) aqueous sodium hydroxide and then with brine, dried and evaporated to yield an oily residue. Crystallization of the residue from cyclohexane-hexane gave [(5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)amino]acetaldehyde dimethylacetal (2.41 g), mp 132°-132.5° C.; Anal. Calcd for C16H19N3O2 : C, 67.34% H, 6.71% N, 14.73%, Found: C, 67.11% H, 6.69% N, 14.40%.

Workup

  1. customThe precipitate which formed in the beginning
  2. dissolutionredissolved
  3. customto afford a brown solution
  4. washwashed with 10% (v/v) aqueous sodium hydroxide
  5. dry with materialwith brine, dried
  6. customevaporated
  7. customto yield an oily residue
  8. customCrystallization of the residue from cyclohexane-hexane

Sources & evidence

ORD record
ord-9e5d8b0d96d44d1b8b37b71635b00d3a
Source dataset
uspto-grants-1985_06
Patent number
US04521534

Reaction notes

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