N-bromobutanimide → HCID 178517109, compound

HRID 466989Notes

Reaction equation

HRID 466989 reaction equation
[NH:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[N:3]1[CH2:13][CH:14]=[CH2:15].[Br:16]N1C(=O)CCC1=O>O1CCCC1>[Br:16][CH2:15][CH:14]1[CH2:13][N:3]2[C:4](=[O:12])[NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]2=[N:1]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178456605HCID 178456605, compound

Product 1

HCID 178517109HCID 178517109, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dihydro-4-imino-3-allyl-2(1H) -quinazolinone (10 g, 50 mmol) in tetrahydrofuran (70 mL) was added N-bromosuccinimide (9.0 g, 50 mmol). The mixture was then stirred at room temperature for 25 minutes. The solid was collected by filtration and recrystallized from THF to afford 2-bromomethyl-2,3-dihydro-imidazo[1,2-c]quinazolin-5(6H)-one (11.18 g, 95%), mp 213°-214° C. 1H NMR (300 MHz, DMSO-d6): δ3.67(m, 2H, CH2), 3.74 (q, 1H, CH), 3.94 (t, 1H, CH), 4.57 (m, 1H, =CH), 7.07 (q, 2H, Ar--H), 7.51 (t, 1H, Ar--H), 7.78 (d, 1H, Ar--H), 10.65 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): d 47.80, 64.16, 110.27, 115.13, 122.23, 125.80, 133.59, 139.97, 147.47, 153.98, 206.07. Anal. Calcd for C11H10N3OBr: C, 47.16; H, 3.59; N, 15.00. Found: C, 47.09; H, 3.41; N, 14.90.

Workup

  1. filtrationThe solid was collected by filtration
  2. customrecrystallized from THF

Sources & evidence

ORD record
ord-eef5847528144f3f99b2616a2c931231
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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