Ammonia → HCID 178444427, compound

HRID 1650585Notes

Reaction equation

HRID 1650585 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[O:21][C:22](=[O:39])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C@@H:35]([CH3:38])[CH2:36][CH3:37])=[CH:25][CH:24]=1.[Cu][C:41]#[N:42].N>CN1CCCC1=O>[C:41]([C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[O:21][C:22](=[O:39])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C@@H:35]([CH3:38])[CH2:36][CH3:37])=[CH:25][CH:24]=1)#[N:42]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 178418546HCID 178418546, compoundHCID 178444425HCID 178444425, compound

Product 1

HCID 178444427HCID 178444427, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 2 g of (S)-4-(6-methyloctyloxy)benzoic acid 2-bromo-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl ester, 0.5 g of anhydrous copper(I) cyanide and 50 ml of absolute 1-methyl-2-pyrrolidone was heated to 185° C. on a oil-bath for 2 hours. The cooled mixture was subsequently treated with 50 ml of 15% ammonia solution and stirred for 30 minutes. Thereafter, the reaction mixture was extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 250 ml of water each time, dried over magnesium sulphate and concentrated. Chromatography of the residue on silica gel with toluene/hexane (vol. 1:1) gave 0.1 g of (S)-4-(6-methyloctyloxy)benzoic acid 2-cyano-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl ester; m.p. (C-Ch) 80° C., transition S*C -Ch 50° C. (monotropic), cl.p. (Ch-I) 120° C.

Workup

  1. extractionThereafter, the reaction mixture was extracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases were washed twice with 250 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e557efde77342299c1f6bc85f8a6126
Source dataset
uspto-grants-1990_05
Patent number
US04925278

Reaction notes

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