Acetic Acid → HCID 22220594, compound

HRID 433130Notes

Reaction equation

HRID 433130 reaction equation
C(O)(=O)C.Br.C(OP([N:14]1[CH2:27][CH2:26][N:25]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N+:37]([O-:39])=[O:38])(=[O:30])=[O:29])[CH2:24][CH2:23][CH2:22][C:21]([F:41])([F:40])[CH2:20][CH2:19][CH2:18][N:17]([S:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[N+:51]([O-:53])=[O:52])(=[O:44])=[O:43])[CH2:16][CH2:15]1)(=O)OCC)C>C(OCC)C>[F:41][C:21]1([F:40])[CH2:22][CH2:23][CH2:24][N:25]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N+:37]([O-:39])=[O:38])(=[O:30])=[O:29])[CH2:26][CH2:27][NH:14][CH2:15][CH2:16][N:17]([S:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[N+:51]([O-:53])=[O:52])(=[O:43])=[O:44])[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 46180615HCID 46180615, compound

Product 1

HCID 22220594HCID 22220594, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetic acid (10 ml), saturated with anhydrous hydrogen bromide (gas) was added to [11,11-difluoro-1,7-bis(2-nitro-benzenesulfonyl)-1,4,7-triaza-cyclotetradec-4-yl]-phosphonic acid diethyl ester (311 mg, 0.41 mmol) contained in round-bottomed flask closed by glass stopper. The resulting mixture was allowed to stir for 18 hours at room temperature and then diethyl ether (50 ml) was added. The white precipitate which formed was allowed to settle to the bottom of the flask and the diethyl ether solution was decanted off. This white solid was re-dissolved in methanol, stirred with K2CO3 (solid) for 30 mins and the mixture was diluted with 100-ml ethyl acetate. The solids were removed by filtration and the filtrates were evaporated to give the title compound (239 mg, 94%) as white form.

Workup

  1. customcontained in round-bottomed flask
  2. customclosed by glass stopper
  3. customThe white precipitate which formed
  4. customthe diethyl ether solution was decanted off
  5. dissolutionThis white solid was re-dissolved in methanol
  6. stirringstirred with K2CO3 (solid) for 30 mins
  7. additionthe mixture was diluted with 100-ml ethyl acetate
  8. customThe solids were removed by filtration
  9. customthe filtrates were evaporated

Sources & evidence

ORD record
ord-9c9a6795f0394e49be21f6ffd6a011b1
Source dataset
uspto-grants-2003_12
Patent number
US06667320B2

Reaction notes

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