Triethylamine → HCID 68419334, compound

HRID 506438Notes

Reaction equation

HRID 506438 reaction equation
[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=O)[CH2:3][CH2:2]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C1COCC1>[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]2[O:15][C:14](=[O:16])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[N:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 68419867HCID 68419867, compound

Product 1

HCID 68419334HCID 68419334, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Cyclopropyl-1,2,3-thiadiazol-5-ylcarbonylamino)benzoic acid (0.77 g; 2.7 mmols), triethylamine (0.54 g; 5.3 mmols) and 2-chloro-1-methylpyridinium iodide (0.82 g; 3.2 mmols) were dissolved or suspended in THF (15 ml), followed by stirring at room temperature for 10 hours. Subsequently, insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. Crystals thus formed were washed with methanol to obtain 0.63 g of 2-(4-cyclopropyl-1,2,3-thiadiazol-5-yl)-4H-3,1-benzoxazin-4-one.

Workup

  1. customSubsequently, insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customCrystals thus formed
  4. washwere washed with methanol

Sources & evidence

ORD record
ord-2cc3b8b9138747f2a57d265b4af6cc5a
Source dataset
uspto-grants-2010_08
Patent number
US07786040B2

Reaction notes

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