Phosgene → HCID 54505771, compound

HRID 2081220Notes

Reaction equation

HRID 2081220 reaction equation
[C:1](Cl)(Cl)=[O:2].[F:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[C:12]([CH2:16][CH2:17][NH:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])[C:24]=1[CH3:25])=[CH:11]2>ClCCl.ClCCl.CO>[F:5][C:6]1[C:14]2[N:13]([CH3:15])[C:12]3[CH2:16][CH2:17][N:18]([CH2:19][C:20]4[N:21]=[CH:22][N:23]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:27])=[O:28])[C:24]=4[CH3:25])[C:1](=[O:2])[C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 19799241HCID 19799241, compound

Product 1

HCID 54505771HCID 54505771, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of phosgene (12.5% v/v in toluene; 4 ml) in dichloromethane (4 ml) was added a solution of 4-[[[2-(7-fluoro-1-methyl-1H-indol-2-yl)ethyl]amino]methyl]-N,N,5-trimethyl-1H-imidazole-1-sulphonamide (100 mg) in dichloromethane (4 ml), and the resulting mixture was stirred for 1 h. The solvent was removed in vacuo, and the residue was dissolved in dichloromethane (5 ml). Aluminium chloride (68 mg) was added, and the mixture was heated at reflux for 3 h. The cooled mixture was then poured into 2M sodium hydroxide solution (80 ml) and extracted with dichloromethane (2×50 ml). The combined, dried organic extracts were evaporated in vacuo to leave a solid which was dissolved in dichloromethane:methanol (1:1; 50 ml) and adsorbed onto silica. Purification by FCC eluting with System A (200:8:1) gave a solid (21 mg) which was triturated with ether to give the title compound (14 mg), m.p. 162°-166°.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. additionAluminium chloride (68 mg) was added
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 3 h
  6. additionThe cooled mixture was then poured into 2M sodium hydroxide solution (80 ml)
  7. extractionextracted with dichloromethane (2×50 ml)
  8. customdried organic extracts were evaporated in vacuo
  9. customto leave a solid which
  10. customPurification by FCC
  11. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-35f418a74ee3448e868b4c30425e0fc1
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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