Diethyl Malonate → HCID 86743278, compound

HRID 1722060Notes

Reaction equation

HRID 1722060 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]3[CH2:33][CH:32]([C:34]#[N:35])[CH2:31][C:29]=3[N:30]=2)=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(O[C:43]1[CH:48]=[CH:47][C:46]([C:49]2(C(OCC)=O)N(C([O-])=O)C=CS2)=[CH:45][CH:44]=1)CCCCC.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C(OCC)(=O)CC(OCC)=O.BrCCCCCCC.[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]3[CH2:33][C:32]([C:34]#[N:35])([CH2:47][CH2:48][CH2:43][CH2:44][CH2:45][CH2:46][CH3:49])[CH2:31][C:29]=3[N:30]=2)=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

11

Reactant 8

HCID 7761Diethyl MalonateHCID 7912DiisopropylamineHCID 123691-BromoheptaneHCID 25517Ammonium ChlorideHCID 85570p-ToluenesulfonateHCID 86743279HCID 86743279, compoundHCID 86743280HCID 86743280, compoundHCID 178418339Butyllithium

Product 1

HCID 86743278HCID 86743278, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

6.1 ml of a 15% solution of butyllithium in hexane are added to a mixture of 1.4 ml of diisopropylamine in 10 ml of THF at -20°. 3.3 of g of 2-(4-n-hexyloxyphenyl)-5-cyano-5,6-dihydro-4-H-cyclopenta[d]thiazole (which can be prepared from ethyl 2-(4-n-hexyloxyphenyl)-thiazole-2,3-dicarboxylate by (a) reduction of the carbonyl groups, (b) conversion into the tosylate, (c) cyclization by reaction with diethyl malonate, (d) saponification and decarboxylation and (e) introduction of the nitrile group) in 10 ml of THF are then added at -60°, the mixture is stirred for 15 minutes, 1.8 g of 1-bromoheptane are then added and the mixture is stirred at -60° for a further 30 minutes and stirred overnight at room temperature. 10% ammonium chloride solution is added and the mixture is then worked up in the customary manner to give 2-(4-n-hexyloxyphenyl)-5-cyano-5-n-heptyl-5,6-dihydro-4-H-cyclopenta[d]thiazole.

Workup

  1. additionare then added at -60°
  2. stirringthe mixture is stirred at -60° for a further 30 minutes
  3. stirringstirred overnight at room temperature

Sources & evidence

ORD record
ord-809565e6b3194b1fb3fb9b8d347b8f4a
Source dataset
uspto-grants-1989_08
Patent number
US04853149

Reaction notes

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