Triethylamine → HCID 18989498, compound

HRID 2395630Notes

Reaction equation

HRID 2395630 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1)#[N:2].Br.[Br:13][CH2:14][CH2:15][CH2:16][NH:17][C@H](C(O)=O)C.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([NH:17][CH2:16][CH2:15][CH2:14][Br:13])=[O:11])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 86748756HCID 86748756, compound

Product 1

HCID 18989498HCID 18989498, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10.0 g (0.07 mole) 4-cyanophenyl isocyanate in 200 mL methylene chloride at 23° C. was added with stirring 15.2 g (0.07 mole) 3-bromopropylalanine hydrobromide. To this was added 7.08 g (0.07 mole) triethylamine via syringe. After the addition was complete the reaction was allowed to proceed for one hour. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate (2×50 mL), dilute aqueous hydrochloric acid, dried (Na2SO4) and concentrated to give 13.8 g (85%) of desired N-4-cyanophenyl-N'-3-bromopropyl urea contaminated with 15% isocyanate dimer.

Workup

  1. additionAfter the addition
  2. washwashed with saturated sodium bicarbonate (2×50 mL), dilute aqueous hydrochloric acid
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64e49f2da35c4279af3c77aaf8958c05
Source dataset
uspto-grants-1996_02
Patent number
US05489594

Reaction notes

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