Ammonia → 126101-04-0

HRID 344746Notes

Reaction equation

HRID 344746 reaction equation
[O:1]=[C:2]1[CH2:6][N:5]2[C:7](=[O:10])[CH2:8][CH2:9][CH:4]2[N:3]1[CH2:11][C:12]([O:14]CC)=O.[NH3:17]>CO>[O:1]=[C:2]1[CH2:6][N:5]2[C:7](=[O:10])[CH2:8][CH2:9][CH:4]2[N:3]1[CH2:11][C:12]([NH2:17])=[O:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10105098HCID 10105098, compound

Product 1

HCID 3079591126101-04-0Yield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2,5-dioxohexahydropyrrolo[1,2-a]imidazole-1-acetate (1.4 g, 6.18 mmol), in methanol (25 ml) was saturated with ammonia at 0° C. After stirring at room temperature for 16 hours the precipitate was collected, washed with methanol and dried to yield 0.9 g (75%) of the title compound, m.p. 182°-185° C. NMR (DMSO-d6): deltaH =7.50 and 7.10 (2s, 2H, CONH2); 5.25 (c.a. 1H, N--CH--N); 3.94 and 3.55 (ABq, J=16 Hz, 2H, N--CH2CO); 3.85 and 3.70 (ABq, J=16.5 Hz, 2H, N--CH2CONH2); 2.90 and 1.90 (c.a., 4H, CH2CH2). MS (E.I., 70 eV, 1.5 mA) m/z=139 (M--CH2CONH2)+.

Workup

  1. customwas collected
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-57247d597beb4bd181067387e60ef7b9
Source dataset
uspto-grants-1991_10
Patent number
US05053422

Reaction notes

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