4-Chlorophenyl Isocyanate → HCID 13934776, compound

HRID 1788908Notes

Reaction equation

HRID 1788908 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>O1CCCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([N:17]2[CH2:18][CH2:19][N:14]([C:3]3[C:4](=[O:13])[C:5]4[C:10]([C:11](=[O:12])[C:2]=3[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:15][CH2:16]2)=[O:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 137185842-Methyl-3-(1-piperazinyl)-1,4-naphthalenedione

Product 1

HCID 13934776HCID 13934776, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 150 mg of 3-methyl-2-piperazinyl-1,4-naphthoquinone in 50 ml of tetrahydrofuran was treated with a solution of 100 mg of 4-chlorophenylisocyanate in 10 ml of tetrahydrofuran. This mixture was stirred 1/2 hour, then evaporated in vacuo and the residue taken up in dichloromethane and filtered. The filtrate was evaporated and the residue recrystallized from dichloromethane/hexane, giving 200 mg of the desired product, mp 190°-192° C.

Workup

  1. customevaporated in vacuo
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-9932b54276624110a863e2acdaabdbe2
Source dataset
uspto-grants-1987_08
Patent number
US04686220

Reaction notes

Loading…