Urea → HCID 54031214, compound

HRID 1905140Notes

Reaction equation

HRID 1905140 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([O:33][CH:34]([CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:35])[CH:12]=[C:13]2[C:18]=1[CH:17]([C:19](OC1C=CC([N+]([O-])=O)=CC=1)=[O:20])[CH2:16][C:15]([CH3:32])([CH3:31])[CH2:14]2)C1C=CC=CC=1.[NH2:45][C:46]([NH2:48])=[O:47].[H-].[Na+]>CS(C)=O>[OH:8][C:9]1[CH:10]=[C:11]([O:33][CH:34]([CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH3:35])[CH:12]=[C:13]2[C:18]=1[CH:17]([C:19]([NH:45][C:46]([NH2:48])=[O:47])=[O:20])[CH2:16][C:15]([CH3:32])([CH3:31])[CH2:14]2

Participants

5

Reactant 3

HCID 1176UreaHCID 24758Sodium hydrideHCID 13985546HCID 13985546, compound

Product 1

HCID 54031214HCID 54031214, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

By reacting 1.2 g. (2 mmole) p-nitrophenyl 8-benzyloxy-3,3-dimethyl-6-(5-phenyl-2-pentyloxy)tetralin-1-carboxylate, 0.3 g. (5 mmole) urea and 0.248 g. (10 mmole) sodium hydride in 12 ml. dimethylsulfoxide at room temperature for one hour and isolation of product by the method of Example 89, Part B and removal of benzyl group by hydrogenolysis by the procedure of Example 89, Part C affords the pure title compound in 36% overall yield. 1H-NMR (CDCl3) ppm (delta): 0.77 (s, 3H), 1.1 (m, 8H), 1.7 (m, 4H), 2.5 (m, 4H), 3.6 (m, 1H), 4.16 (m, 1H), 5.7 (s, 1H), 6.1 (s, 2H), 7.1 (s, 5H), 8.2 (s, 2H).

Workup

  1. customisolation of product by the method of Example 89, Part B and removal of benzyl group by hydrogenolysis by the procedure of Example 89, Part C

Sources & evidence

ORD record
ord-73d12947d1164aa68f2e00943a3c4562
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

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