Ammonia → HCID 57413725, compound

HRID 1428975Notes

Reaction equation

HRID 1428975 reaction equation
C([N:4]([CH2:8]C)C(C)C)(C)C.[Br:10][C:11]1[S:15][CH:14]=[C:13](C(O)=O)[CH:12]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.[NH3:36]>O1CCOCC1>[Br:10][C:11]1[S:15][CH:14]=[C:13]([NH:36][C:8]([NH2:4])=[O:26])[CH:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 57413725HCID 57413725, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Under nitrogen atmosphere N,N-diisopropylethylamine (0.390 g, 3 mmol) was added to the solution of 5-bromothiophene-3-carboxylic acid (0.207 g, 1 mmol) and diphenylphosphoryl azide (DPPA) (0.330 g, 1.2 mmol) in dioxane (5 ml) at rt. After stirring for 30 min, the mixture was heated at 85 for 1.5 h. After the mixture cooled down to rt, 0.5 M of ammonia solution in dioxane (12 ml) was added. 30 min's later, the solvents was removed and the resulting residue was purified by silica gel chromography with CH2Cl2/MeOH combinations to give (5-bromo-3-thienyl)urea (0.072 g) in 32% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.80 (s, 1H), 7.09 (s, 2H), 5.87 (s, 2H). MS (ESI): found [M+H]+, 223.0.

Workup

  1. temperaturethe mixture was heated at 85 for 1.5 h
  2. custom30 min's later, the solvents was removed
  3. customthe resulting residue was purified by silica gel chromography with CH2Cl2/MeOH combinations

Sources & evidence

ORD record
ord-83eb30ff4b724f53bf95cee2ef1188a8
Source dataset
uspto-grants-2015_01
Patent number
US08937167B2

Reaction notes

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