Tert-Butyl nitrite → HCID 178458180, compound

HRID 54919Notes

Reaction equation

HRID 54919 reaction equation
N(OC(C)(C)C)=O.[CH2:8]([O:11][C:12]1[CH:24]=[CH:23][C:15]2[N+:16]([O-:22])=[C:17](N)[N:18]=[N+:19]([O-:20])[C:14]=2[CH:13]=1)[CH:9]=[CH2:10]>CN(C=O)C>[CH2:8]([O:11][C:12]1[CH:24]=[CH:23][C:15]2[N+:16]([O-:22])=[CH:17][N:18]=[N+:19]([O-:20])[C:14]=2[CH:13]=1)[CH:9]=[CH2:10]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitrite2×HCID 135624029121135-28-2

Product 1

HCID 178458180HCID 178458180, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of t-butyl nitrite (271 mg, 0.312 ml, 2.63 mmol) in DMF (15 ml) at 60°-65° C. was added 7-allyloxy-3-amino-1,2,4-benzotriazine- 1,4-dioxide 23 (205 mg, 0.875 mmol) in small portions over 5 min. After 30 min additional t-butyl nitrite (271 mg, 0.312 ml, 2.63 mmol) was added, and shortly thereafter the deep red solution effervesced and lightened appreciably in color over a period of a few minutes. After an additional 30 min the resultant orange solution was reduced under vacuum to a brown solid which was sequentially flash chromatographed (10% EtOAc/CH2Cl2) and crystallized (CH2Cl2 /petroleum ether) to give 72 mg (38% yield) of the product 24 as light orange crystals, mp 147°-148° C.

Workup

  1. waitlightened appreciably in color over a period of a few minutes
  2. customchromatographed (10% EtOAc/CH2Cl2)
  3. customcrystallized (CH2Cl2 /petroleum ether)

Sources & evidence

ORD record
ord-62c0b4d11e1444f5a2579c050ac59fd7
Source dataset
uspto-grants-1997_04
Patent number
US05624925

Reaction notes

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