Benzoyl isocyanate → Urea, (1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-

HRID 2072372Notes

Reaction equation

HRID 2072372 reaction equation
O=C1C2C(=CC=CC=2)C(N)CC1.O=C1C2C(=CC=CC=2)C(NC=O)CC1.C(N=C=O)(=O)C1C=CC=CC=1.C([NH:46][C:47]([NH:49][CH:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:53](=[O:60])[CH2:52][CH2:51]1)=[O:48])(=O)C1C=CC=CC=1>>[O:60]=[C:53]1[C:54]2[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:50]([NH:49][C:47]([NH2:46])=[O:48])[CH2:51][CH2:52]1

Participants

5

Reactant 4

HCID 78210Benzoyl isocyanateHCID 137386604-amino-3,4-dihydro-2H-naphthalen-1-oneHCID 205373021-Benzoyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)ureaHCID 20537306N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)formamide

Product 1

HCID 3628438Urea, (1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-

Procedure

In the manner described in Example 5, (+)-1,2,3,4- tetrahydro-4-oxo-1-naphthylamine, which is obtaind by acid hydrolysis (refluxing in HC1)of (-)-N-(1,2,3,4-tetrahydro-4- oxo-1-naphthyl)formamide followed by neutralization, is allowed to react with benzoyl isocyanate. The resulting 1-benzoyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)urea is then hydrolyzed with alkali as in Example 6 to afford (-)-1,2,3,4-tetrahydro-4-oxo-1-naphthylurea.

Workup

  1. customis obtaind by acid hydrolysis (

Sources & evidence

ORD record
ord-7e6ceabec91e43dd8f9267c54e6c0d73
Source dataset
uspto-grants-1977_09
Patent number
US04051183

Reaction notes

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