Triethylamine → HCID 86643481, compound

HRID 1423363Notes

Reaction equation

HRID 1423363 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13](O)=[O:14])=[CH:4][C:3]=1[O:16][CH3:17].C(N(CC)CC)C.C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]([N:39]=[N+:40]=[N-:41])=[O:14])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68667474HCID 68667474, compound

Product 1

HCID 86643481HCID 86643481, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 3-(4-bromo-3-methoxyphenyl)thiophene-2-carboxylic acid (2.23 g, 7.13 mmol) in benzene (28.5 mL) was treated with triethylamine (1.39 ml, 9.98 mmol) and diphenylphosphoryl azide (1.96 g, 7.13 mmol). The mixture was stirred for 20 h, then the volatiles were removed ant the residue was purified by column chromatography on silica gel (eluent: toluene) to afford the title (1.63 g, 68%). LCMS (ES+) m/z 310, 312 (M+H−N2)+.

Workup

  1. customthe volatiles were removed ant the residue
  2. customwas purified by column chromatography on silica gel (eluent: toluene)
  3. customto afford the title (1.63 g, 68%)

Sources & evidence

ORD record
ord-13440d4b68d249f09990e127e0c1a443
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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