1-Naphthylamine → 2,3-Dibromo-N-[(naphthalen-1-yl)carbamoyl]propanamide

HRID 259168Notes

Reaction equation

HRID 259168 reaction equation
[Br:1][CH:2]([CH2:8][Br:9])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[NH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[C:11]1([NH:10][C:6]([NH:5][C:3](=[O:4])[CH:2]([Br:1])[CH2:8][Br:9])=[O:7])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 86401-NaphthylamineHCID 203185382,3-Dibromopropanoyl isocyanate

Product 1

HCID 214232532,3-Dibromo-N-[(naphthalen-1-yl)carbamoyl]propanamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

26.0 g of 2,3-dibromopropionyl isocyanate in 100 ml of toluene are added dropwise at 5 to 10° C to a solution of 14.5 g of 1-aminonaphthalene in 200 ml of dry benzene. After stirring for 2 hours at 20° C., the reaction product is diluted with petroleum ether, filtered and dried. Yield: 35.0 g, m.p: 194° - 195° C. (decomp.).

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-38979f8ec9024ca1ad88a49cd5890dd4
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

Loading…