Diethyl Ether → HCID 20153940, compound

HRID 2414119Notes

Reaction equation

HRID 2414119 reaction equation
[CH2:1]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]#[N:19])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].[CH2:27]([O:29]CC)[CH3:28]>>[CH2:1]([C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:27](=[O:29])[CH3:28])[C:9]#[N:10])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][C:14]([N:17]([C:20](=[O:22])[CH3:21])[C:18]#[N:19])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 169119Cyanamide, (methylenedi-4,1-phenylene)bis-

Product 1

HCID 20153940HCID 20153940, compound

Procedure

124.1 g (0.5 mol) of 4,4'-methylene-bis-(phenylcyanamide) and 510.5 g (1.0 mol+400% excess) of acetic anhydride are reacted at 73°-83° C. for 4 hours and 10 minutes, 465 ml of diethyl ether are then added and the mixture is cooled. The suspension is filtered with suction and the residue is dried at 50° C. in vacuo to give 139.6 g (84.0% of theory) of a crystalline product which, after recrystallisation from toluene, has a melting point of 134°-136° C.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationThe suspension is filtered with suction
  3. customthe residue is dried at 50° C. in vacuo
  4. customto give 139.6 g (84.0% of theory) of a crystalline product which
  5. customafter recrystallisation from toluene

Sources & evidence

ORD record
ord-0b28ccbc32354e868c5ef6cd522fb37b
Source dataset
uspto-grants-1988_01
Patent number
US04721770

Reaction notes

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