Sodium hydride → HCID 18957139, compound

HRID 2379468Notes

Reaction equation

HRID 2379468 reaction equation
[H-].[Na+].ClC(Cl)(O[C:7](=[O:13])OC(Cl)(Cl)Cl)Cl.[CH:15]1([NH:21][C:22]2[N:23]=[N:24][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:26]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:39][CH:40]([C:42]1[CH:48]=[CH:47][CH:46]=[C:45]([CH:49]([CH3:51])[CH3:50])[C:43]=1[NH2:44])[CH3:41].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:51][CH:49]([C:45]1[CH:46]=[CH:47][CH:48]=[C:42]([CH:40]([CH3:41])[CH3:39])[C:43]=1[NH:44][C:7](=[O:13])[N:21]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:22]1[N:23]=[N:24][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:26]=1)[CH3:50]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 32484DiisopropylanilineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 18957138HCID 18957138, compound

Product 1

HCID 18957139HCID 18957139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of a 60% dispersion of sodium hydride in mineral oil (0.2648 g, 0.0066 mol) in a solution of triphosgene (0.4583 g, 0.001544 mol) and N-cyclohexyl-2-dodecyl-2H-tetrazol-5-amine (1.5540 g, 0.0046313 mol) in anhydrous tetrahydrofuran (15 mL) under a nitrogen atmosphere was refluxed for 4.5 days. To the mixture was added 2,6-bis(1-methylethyl)aniline (0.88 mL, 0.0047 mol) and diisopropylethylamine (0.89 mL, 0.0051 mol), and the reflux was continued for 7 days. The mixture was rotoevaporated, and the residue partitioned between diethyl ether and saturated sodium bicarbonate. The organic layer was washed with 1M hydrochloric acid and saturated sodium chloride, dried (MgSO4), and rotoevaporated to an oil. The oil was chromatographed on silica gel (430 g, 230-400 mesh) using PET ether-ethyl acetate (30:1, 14×400 mL) to give the title compound as an oil, yield 1.4522 g (58%) . 1H NMR (CDCl3): δ 8.8 (s, 1H), 7.3 (dd, 2H), 7.2 (d, 1H), 4.6 (m, 3H), 3.1 (septet, 2H), 2.1 (m, 4H), 1.8 (m, 4H), 1.6 (m, 2H), 1.3 (m, 32H), 0.9 (t, 3H).

Workup

  1. temperaturewas refluxed for 4.5 days
  2. customthe residue partitioned between diethyl ether and saturated sodium bicarbonate
  3. washThe organic layer was washed with 1M hydrochloric acid and saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. customThe oil was chromatographed on silica gel (430 g, 230-400 mesh)

Sources & evidence

ORD record
ord-0c8242810bb5409a90752e93be28feba
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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