Triethylamine → (3-Iodophenyl)(isocyano)methyl 4-methylphenyl sulfone

HRID 32564Notes

Reaction equation

HRID 32564 reaction equation
O=P(Cl)(Cl)Cl.[I:6][C:7]1[CH:8]=[C:9]([CH:13]([NH:24][CH:25]=O)[S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.CCN(CC)CC.CCOC(C)=O>C1COCC1.C(Cl)Cl.O>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([CH:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([I:6])[CH:8]=2)[N+:24]#[C-:25])(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 85929703{(3-Iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide2×

Product 1

HCID 17965763(3-Iodophenyl)(isocyano)methyl 4-methylphenyl sulfone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

POCl3 (3.05 mL) was added to a stirred solution of {(3-iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 52) (6.23 g) in dry THF (35 mL) at 25° C. and stirred for 5 minutes. The reaction mixture was cooled to 0° C. and Et3N (13.7 mL) was added dropwise over 45 minutes, keeping the internal temperature below 10° C. The reaction mixture was allowed to stir at 5-10° C. for a further 45 minutes. EtOAc (140 mL) and water (140 mL) was added and then stirred for 5 minutes. The organic phase was washed with water (2×140 mL), NaHCO3 (sat. aq., 140 mL) and then brine (140 mL). The organic phase was concentrated in vacuo to afford a dark brown gum. This was then passed through a pad of silica washing with DCM and concentrated in vacuo to afford a dark brown gum (ca. 70% pure 3.5 g, 58%);

Workup

  1. customthe internal temperature below 10° C
  2. stirringto stir at 5-10° C. for a further 45 minutes
  3. stirringstirred for 5 minutes
  4. washThe organic phase was washed with water (2×140 mL), NaHCO3 (sat. aq., 140 mL)
  5. concentrationThe organic phase was concentrated in vacuo
  6. customto afford a dark brown gum
  7. concentrationconcentrated in vacuo
  8. customto afford a dark brown gum (ca. 70% pure 3.5 g, 58%)

Sources & evidence

ORD record
ord-42a69b4f90824b5d9ea6643810ee667b
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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