Hydrogen Bromide → Urea, (1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-

HRID 1155643Notes

Reaction equation

HRID 1155643 reaction equation
[CH:1]1([NH:11][C:12]([NH2:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br.C(C(C)=[O:19])C.O=O>C(O)(=O)C.O>[O:19]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]([NH:11][C:12]([NH2:14])=[O:13])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 977OxygenHCID 6569Methyl Ethyl KetoneHCID 13037020(1,2,3,4-Tetrahydronaphthalen-1-yl)urea

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-1-naphthylurea (1.9 g), cobaltous acetate tetrahydrate (1.08 g), 30% hydrobromic acid in acetic acid (0.9 ml) and a 1:1 mixture of methyl ethyl ketone: acetic acid (30 ml) is shaken in a pressure vessel under 31 psig of oxygen for 7.5 hours. The vessel is then vented, the contents are mixed with an equal volume of water and extracted with chloroform (2×25 ml). The combined chloroform extracts are dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo to afford 2.34 g solid. The solid is washed with cold methanol (30 ml) to afford 0.75 g of title compound, m.p. 210° C. to 214° C.

Workup

  1. extractionextracted with chloroform (2×25 ml)
  2. dry with materialThe combined chloroform extracts are dried over anhydrous magnesium sulfate
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4424b3f02d0b476fb465759547245543
Source dataset
uspto-grants-1982_06
Patent number
US04332724

Reaction notes

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