Tetrahydrofuran → HCID 178524281, compound

HRID 565172Notes

Reaction equation

HRID 565172 reaction equation
O1CCCC1.[O:6]([C:13]([C:15]1[C:23]2[N:22]=[N:21][NH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1)=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(OC(Cl)(Cl)Cl)[O:25][C:26]([Cl:29])(Cl)Cl>C(OCC)(=O)C>[C:26]([Cl:29])(=[O:25])[NH2:20].[O:6]([C:13]([C:15]1[C:23]2[N:22]=[N:21][NH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1)=[O:14])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 94429TriphosgeneHCID 178524281HCID 178524281, compound

Product 2

HCID 68048Carbamic chlorideHCID 178524281HCID 178524281, compoundYield 292.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (75 mL) solution of phenoxycarbonylbenzotriazole (19.1 g) was dropped into an ethyl acetate solution (100 mL) of bis(trichloromethyl) carbonate (9.5 g) at 10° C. The resultant solution was stirred at 40° C. for 3 hrs. After the solvent was distilled away at reduced pressure, 200 mL of hexane were added to the concentrated residue, and the material was stirred for 1 hr. The crystals were filtered out and dried to obtain carbamoyl chloride of phenoxycarbonylbenzotriazole (to be abbreviated as PBT-COCl hereinafter) (22.4 g).

Workup

  1. distillationAfter the solvent was distilled away at reduced pressure, 200 mL of hexane
  2. additionwere added to the concentrated residue
  3. filtrationThe crystals were filtered out
  4. customdried

Sources & evidence

ORD record
ord-a9dd699dccc84ac3a405a19943fef869
Source dataset
uspto-grants-2001_01
Patent number
US06171772B2

Reaction notes

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