Trityl chloride → HCID 18461285, compound

HRID 2303909Notes

Reaction equation

HRID 2303909 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[C:31]1([C:37](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C.O1CCCC1>CN(C)C=O>[CH3:1][N:2]([C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[N:26][N:25]([C:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:24]=3)=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178486015HCID 178486015, compound

Product 1

HCID 18461285HCID 18461285, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of t-butyl N-methyl-N-[2-nitro-5-(4-tetrazol-5-ylphenoxy)phenyl]carbamate (3.22 g), triphenylmethyl chloride (2.18 g), triethylamine (0.79 g), anyhdrous tetrahydrofuran (30 ml) and anhydrous N,N-dimethylformamide was stirred at ambient temperature for 24 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=5/1 as the eluant to give the title compound (3.15 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-30ef956c917b4ff4aade4401989557a7
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…