3-(Methylthio)phenyl isocyanate → 4-[3-(3-Methylsulfanylphenyl)-1-spiro[5.5]undec-3-yl-ureidomethyl]benzoic acid methyl ester

HRID 1814706Notes

Reaction equation

HRID 1814706 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][C:15]3([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[CH3:24][S:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]([CH:12]2[CH2:17][CH2:16][C:15]3([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][CH2:13]2)[C:33]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([S:25][CH3:24])[CH:27]=2)=[O:34])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 1414183-(Methylthio)phenyl isocyanate2×HCID 235501414-(Spiro[5.5]undec-3-ylaminomethyl)benzoic acid methyl ester

Product 1

HCID 235501374-[3-(3-Methylsulfanylphenyl)-1-spiro[5.5]undec-3-yl-ureidomethyl]benzoic acid methyl esterYield 44.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above 4-(spiro[5.5]undec-3-ylaminomethyl)benzoic acid methyl ester (1.02 g, 3.2 mmol) was added acetonitrile (50 mL) and 3-(methylthio)phenylisocyanate (668 mg, 4 mmol). Upon stirring for 2 days, the reaction appeared incomplete as shown by HPLC, so another portion of 3-(methylthio)phenylisocyanate (240 mg) was added. After stirring for 2 hours the solvent was evaporated. The residue was taken up in dichloromethane (2 mL) and purified by chromatography on silica using dichloromethane as eluent affording 4-[3-(3-methylsulfanylphenyl)-1-spiro[5.5]undec-3-yl-ureidomethyl]benzoic acid methyl ester (680 mg).

Workup

  1. stirringAfter stirring for 2 hours the solvent
  2. customwas evaporated
  3. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-27a0c6dc76034dc8923976f507f68ab0
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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