Ethylamine → HCID 18006604, compound

HRID 456398Notes

Reaction equation

HRID 456398 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10]C)=[C:2]=[O:3].[CH2:12]([NH2:14])[CH3:13].B(Br)(Br)Br>ClCCl>[CH2:12]([NH:14][C:2]([NH:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])=[O:3])[CH3:13]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 25134Boron tribromideHCID 69695Benzene, 1-isocyanato-2-methoxy-

Product 1

HCID 18006604HCID 18006604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-isocyanato-2-methoxybenzene (0.32 g, 2.15 mmol) and ethylamine (1 mL) in dichloromethane (15 mL) was stirred at room temperature for 2 days. Then the volatiles were removed in vacuo. The residue was redissolved in dichloromethane (15 mL), and boron tribromide (BBr3) (1 M in dichloromethane (CH2Cl2), 6.5 ml, 6.5 mmol) was added dropwise via syringe under nitrogen. After stirring for 1 h the reaction mixture was diluted with dichloromethane and washed 3 times with water. The product was purified by HPLC (Kromasil column; eluant:acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA) to give subtitle compound (167 mg).

Workup

  1. customThen the volatiles were removed in vacuo
  2. dissolutionThe residue was redissolved in dichloromethane (15 mL)
  3. washwashed 3 times with water
  4. customThe product was purified by HPLC (Kromasil column; eluant:acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA)

Sources & evidence

ORD record
ord-c0cf7942c09b4d96b50eacb2bdf2843a
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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