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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 52421
Notes
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Reaction equation

HRID 52421 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.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-93f368aa25e441c3a83523bec248d8ca
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616706

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes