Acetonitrile → HCID 20134233, compound

HRID 580626Notes

Reaction equation

HRID 580626 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16]Br)=[CH:11][C:10]=1[NH:19][C:20]([NH2:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH:30][CH:31]([CH3:43])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][CH:34]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(#N)C>CCOCC>[CH2:23]([N:30]([CH:31]([CH3:43])[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:38]=1)[CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([NH:19][C:20]([NH2:22])=[O:21])[CH:11]=1)=[O:18])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 19974252HCID 19974252, compoundHCID 20029860HCID 20029860, compound

Product 1

HCID 20134233HCID 20134233, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(4-Benzyloxy-3-ureidophenyl)-2-bromoethanone (3.1 g) and N-benzyl-(2-[4-carbomethoxyphenyl]-1-methylethanamine) (4.85 g) were heated in refluxing acetonitrile (50 ml) for 2 hours. The solution was diluted with an equal volume of ether, filtered and the filtrate diluted further with ether (200 ml). The solution was washed with water, dried and evaporated to give the title compound, mp 140°-145° (ethyl acetate). τ (CDCl3) 9.00 (3H, d, J=6 Hz), 6.70-7.60 (3H, m), 6.0-6.4 (4H, m), 6.20 (3H, s), 4.90 (2H, s), 6.32 (2H, b), 2.1-3.3 (17H, m), 1.20 (1H, d, J=2 Hz).

Workup

  1. filtrationfiltered
  2. additionthe filtrate diluted further with ether (200 ml)
  3. washThe solution was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-20c1ff37edd145d1a48179e8db314541
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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