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Triethylamine → Isopropyl 3(2-chloro-4-fluoro-5-isothiocyanatophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 1476
Notes
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Reaction equation

HRID 1476 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[C:7]([F:30])=[CH:8][C:9]([Cl:29])=[C:10]([N:12]2[C:17](=[O:18])[N:16]([CH3:19])[C:15](=[O:20])[N:14]([CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:13]2=[O:28])[CH:11]=1.C(N(CC)CC)C>O1CCCC1>[Cl:29][C:9]1[CH:8]=[C:7]([F:30])[C:6]([N:5]=[C:1]=[S:2])=[CH:11][C:10]=1[N:12]1[C:17](=[O:18])[N:16]([CH3:19])[C:15](=[O:20])[N:14]([CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:13]1=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 57313385isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 11729649Isopropyl 3(2-chloro-4-fluoro-5-isothiocyanatophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Thiophosgene (0.50 mL, 6.5 mmol) is added over 45 minutes to a solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (2.5 g, 6.5 mmol), and triethylamine (1.8 mL, 13.0 mmol) in tetrahydrofuran. The reaction mixture is stirred at room temperature for 4 hours, diluted with tetrahydrofuran, and filtered. The filtrate is concentrated in vacuo to give the title product as an orange oil which is identified by NMR spectral analyses, Using essentially the same procedure, but using the appropriately substituted 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-2,4,6-trioxo-s-triazine, the following compounds are obtained:

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-abde48b4f1894595a808afe5690eeb6d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726126

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes