HCID 17278316, compound → HCID 13853505, compound

HRID 542493Notes

Reaction equation

HRID 542493 reaction equation
[CH:1]([NH:5][C:6](=[O:18])[NH:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=O)([CH2:3][CH3:4])[CH3:2]>S(=O)(=O)(O)O>[CH:1]([NH:5][C:6]1[O:18][C:10](=[O:12])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[N:7]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 17278316HCID 17278316, compound

Product 1

HCID 13853505HCID 13853505, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 2-(3-sec-butyl-ureido)benzoate (90 mg) was dissolved in 2 ml of concentrated sulfuric acid. The solution was stirred for 21/2 hours and poured onto ice. The ice-quenched mixture was rapidly neutralized with saturated sodium bicarbonate solution. The resulting white precipitate was filtered, dried and recrystallized from ether and petroleum ether, to yield 2-sec-butylamino-4H-3,1-benzoxazin-4-one, m.p. 122°-123° C.; 'H NMR (delta CDCl3): 1.0 (t, 3H, CH3CH2); 1.3 (d, 3H, CH3CH); 1.6 (m, 2H, CH2); 4.0 (m, 1H, CH--N); 7.2, 7.6 8.0 (3m, 4H, ArH). The infrared spectrum of this compound showed maxima at 3290, 1740, 1635 and 1600 cm-1.

Workup

  1. additionpoured onto ice
  2. customThe ice-quenched mixture
  3. filtrationThe resulting white precipitate was filtered
  4. customdried
  5. customrecrystallized from ether and petroleum ether

Sources & evidence

ORD record
ord-acc3cd7a876a436ab90175529f8e929f
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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