Sulfuric Acid → HCID 18607273, compound

HRID 542496Notes

Reaction equation

HRID 542496 reaction equation
S(=O)(=O)(O)O.C(C1C=CC=CC=1[N:16](C(=O)N)[C@H:17]([C:25]([NH2:27])=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OC)=O.[C:31]([O:34][CH2:35]C)(=[O:33])[CH3:32]>>[N:16]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:32]=2[C:31](=[O:33])[O:34][C:35]=1[NH:27][C:25](=[O:26])[C@H:17]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 86741417HCID 86741417, compound

Product 1

HCID 18607273HCID 18607273, compound

Procedure

5 ml of concentrated sulfuric acid was added to 400 mg of 1-N-(2-carbomethoxyphenyl)-carbamoylphenylalanine amide (Preparation IX). The mixture was stirred for 3 hours and poured onto a mixture of ethyl acetate and ice-cold sodium bicarbonate solution. The mixture was extracted with ethyl acetate after neutralization. The organic extract, dried over magnesium sulfate, was evaporated to a solid. Recrystallization from ethyl acetate-hexane yielded 250 mg of N-(4H-3,1-benzoxazin-4-on-2-yl)-phenylalaninamide; m.p. 215°-216° C. 'H NMR 3.0 (m, 2H, PhCH2), 4.5 (m, 1H, NCH), 7.8-8.2 (overlapping peaks, 9H, ArH). IR: 3380, 3180, 1750, 1730, 1660, 1640 cm-1.

Workup

  1. extractionThe mixture was extracted with ethyl acetate after neutralization
  2. dry with materialThe organic extract, dried over magnesium sulfate
  3. customwas evaporated to a solid
  4. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6d551c08621943f69a7ee6680e6a248c
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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