Chloro-N,N-diethylacetamide → 3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-1-(N,N-diethyl)aminocarbonylmethyl-2,4(1H, 3H)-quinazolinedione

HRID 1995646Notes

Reaction equation

HRID 1995646 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([CH3:27])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH3:21])[NH:12][C:11]1=[O:28].[CH2:29]([N:31]([CH2:36][CH3:37])[C:32](=[O:35])[CH2:33]Cl)[CH3:30]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([CH3:27])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH3:21])[N:12]([CH2:33][C:32]([N:31]([CH2:36][CH3:37])[CH2:29][CH3:30])=[O:35])[C:11]1=[O:28]

Participants

5

Reactant 3

HCID 16844Chloro-N,N-diethylacetamideHCID 24758Sodium hydrideHCID 1336033-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-2,4(1H,3H)-quinazolidinedione

Product 1

HCID 128494253-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-1-(N,N-diethyl)aminocarbonylmethyl-2,4(1H, 3H)-quinazolinedioneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A portion (30 mg) of sodium hydride suspension (50%) in mineral oil was added to a stirred solution of 3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-2,4-(1H, 3H)-quinazolinedione (187 mg) in dimethylformamide (10 ml). After addition of N,N-diethyl-chloroacetamide (80 mg), the mixture was stirred at 80° C. for 3 hours. The solvent was evaporated off at reduced pressure, and the residue was extracted with CHCl3. The CHCl3 extract was washed with water, dried over NaSO4 and concentrated. The residue was recrystallized from methanol to give 3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-1-(N,N-diethyl)aminocarbonylmethyl-2,4(1H, 3H)-quinazolinedione (138 mg, 57%) melting at 228°-229° C. MS: M/e, 485(M+), 450. NMR: δ (ppm, CDCl3), 1.38 (9H, m), 2.39 (3H, s), 2.72 (3H, s), 3.45 (4H, q), 4.40 (2H, q), 4.95 (2H, d), 6.75 (1H, s), 7.40 (4H, m).

Workup

  1. customThe solvent was evaporated off at reduced pressure
  2. extractionthe residue was extracted with CHCl3
  3. extractionThe CHCl3 extract
  4. washwas washed with water
  5. dry with materialdried over NaSO4
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-97dbe4138d5f499da30a4d5802381c17
Source dataset
uspto-grants-1983_09
Patent number
US04405623

Reaction notes

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