Triethylamine → HCID 13653173, compound

HRID 1380913Notes

Reaction equation

HRID 1380913 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:16](=[O:17])[N:15]([CH2:18][C:19](O)=[O:20])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[S:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([N:28](CC)CC)C.O.N>C(Cl)Cl.C(OC(Cl)=O)C(C)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:16](=[O:17])[N:15]([CH2:18][C:19]([NH2:28])=[O:20])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[S:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12896473Azane;hydrateHCID 13653165HCID 13653165, compound

Product 1

HCID 13653173HCID 13653173, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a stirred solution of [2-(4-acetoxyphenyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-4-yl]acetic acid (compound No. 26, 4.6 g) and triethylamine (1.8 ml) in CH2Cl2 (45 ml), isobutylchloroformate (1.7 ml) is added dropwise at -12° C. After the addition, the reaction mixture is stirred for 10 minutes at the same temperature. Conc. ammonia water (7.2 ml) is added to the mixture. The mixture is stirred for 30 minutes at room temperature, and washed with saturated sodium hydrogen carbonate solution and N HCl. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo to give 3.5 g (76%) of the titled compound.

Workup

  1. additionAfter the addition
  2. stirringThe mixture is stirred for 30 minutes at room temperature
  3. washwashed with saturated sodium hydrogen carbonate solution and N HCl
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a5687a7b82a43faa32e7d47bf75564b
Source dataset
uspto-grants-1986_04
Patent number
US04584300

Reaction notes

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