Formic Acid → HCID 14722390, compound

HRID 1031699Notes

Reaction equation

HRID 1031699 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.Br.[NH2:12][C:13]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:16]=2[O:15][C:14]=1[Br:36].C(N(CC)CC)C>C(Cl)Cl>[Br:36][C:14]1[O:15][C:16]2[CH:23]=[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:20][C:17]=2[C:18](=[O:19])[C:13]=1[NH:12][CH:1]=[O:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22168211HCID 22168211, compound

Product 1

HCID 14722390HCID 14722390, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.06 g of acetic anhydride and 2.76 g of formic acid were mixed and stirred for 1.5 hours at 40°-45° C. to prepare a mixed acid anhydride. Separately, 5.06 g of 3-amino-2-bromo-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one hydrobromide was suspended in 100 ml of methylene chloride. To the suspension being ice-cooled was added 1.06 g of triethylamine, and the mixture was stirred for 30 minutes at the same temperature. Thereto was added the above mixed acid anhydride, and the resulting mixture was stirred for 1 hour at 20°-25° C. The solvent was removed by distillation under reduced pressure. The residue was mixed with 200 ml of water. The resulting crystal was collected by filtration and recrystallized from ethyl acetate-diisopropyl ether to obtain 4.15 g (yield: 97.6%) of 2-bromo-3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 237°-238° C.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. stirringthe resulting mixture was stirred for 1 hour at 20°-25° C
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionThe residue was mixed with 200 ml of water
  6. filtrationThe resulting crystal was collected by filtration
  7. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-07c3908756294134b42dc0cc2a0a1dd1
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…