Sodium Nitrite → HCID 178526372, compound

HRID 1679287Notes

Reaction equation

HRID 1679287 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][NH:6][C:7]1[CH2:8][C:9](=[O:24])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1>C(O)(=O)C.O>[N:1]([CH2:5][NH:6][C:7]1[CH2:8][C:9](=[O:24])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:3]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 178482314HCID 178482314, compound

Product 1

HCID 178526372HCID 178526372, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium nitrite, 5.9 g (0.086 moles), was added in 3 portions over a period of 30 minutes to a stirred solution of 18.9 g (0.071 m) of 3,5-dihydro-2-methylamino-5-phenyl-4H-1,5-benzodiazepin-4-one in 200 ml of acetic acid. After the addition was completed, the mixture was stirred for 20 minutes at room temperature and was then diluted with water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was crystallized from ether to yield product. Additional material was obtained from the concentrated mother liquors. For analysis, the material was recrystallized from ethyl acetate/hexane, mp 139°-140° C.

Workup

  1. additionAfter the addition
  2. extractionextracted with methylene chloride
  3. washwashed with saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue was crystallized from ether
  7. customto yield product
  8. customAdditional material was obtained from the concentrated mother liquors
  9. customFor analysis, the material was recrystallized from ethyl acetate/hexane, mp 139°-140° C.

Sources & evidence

ORD record
ord-f9bd045e2574400f95199d287dee9b47
Source dataset
uspto-grants-1978_03
Patent number
US04080323

Reaction notes

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