Trimethylsilylacetylene → N-benzoyl-4-ethynyl-3-nitrobenzamide

HRID 1844787Notes

Reaction equation

HRID 1844787 reaction equation
C[Si]([C:5]#[CH:6])(C)C.I[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C[NH:21][C:22](=[O:33])[C:23]1[CH:28]=[CH:27][C:26](I)=[C:25]([N+]([O-])=O)[CH:24]=1.C[Si](C)(C)CC#C>>[C:22]([NH:21][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][C:8]([C:5]#[CH:6])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=1)(=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 66111TrimethylsilylacetyleneHCID 83378Trimethyl-2-propynylsilaneHCID 112085984-Iodo-3-nitrobenzoic acidHCID 207555454-iodo-N-methyl-3-nitrobenzamide

Product 1

HCID 57331455N-benzoyl-4-ethynyl-3-nitrobenzamide

Procedure

Compound I-14, Compound I-15, Compound I-16, Compound I-17, Compound I-18, Compound I-19, Compound I-20, Compound I-21, Compound I-22, Compound I-23, Compound I-24 and Compound I-25 were prepared sequentially according to the methods of Example 14, Example 15 and Example 16, by selecting appropriate amines and trimethylsilylacetylene, using the Compound 4-iodo-3-nitrobenzoic acid (Compound VI-1) as starting material; Compound I-26 was prepared sequentially according to the methods of Example 15 and Example 16, using the compound N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1) and trimethylpropargylsilane as starting materials:

Workup

  1. customwere prepared sequentially
  2. customCompound I-26 was prepared sequentially

Sources & evidence

ORD record
ord-5db980f8b4964d14b4ace38065301a1e
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Reaction notes

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