2-Chloro-6-fluorophenylisothiocyanate → HCID 178496997, compound

HRID 1898345Notes

Reaction equation

HRID 1898345 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[N:22]=[C:23]=S>C(#N)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[NH:22][C:23]1[NH:1][C:2]2[CH:3]=[C:4]([OH:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 265991402-Chloro-6-fluorophenylisothiocyanateHCID 67504371Methyl 4,5-diamino-2-hydroxybenzoate

Product 1

HCID 178496997HCID 178496997, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared following the procedure described for step-2 of intermediate-55 using methyl 4,5-diamino-2-hydroxybenzoate (step-1 of Intermediate-55, 0.700 g, 3.840 mmol), acetonitrile (5.0 mL), 1-chloro-3-fluoro-2-isothiocyanatobenzene (Intermediate-14, 0.700 g, 3.760 mmol) and N,N-di-isopropyl carbodimide (1.0 mL) to afford 0.5 g of the desired product. 1HNMR (DMSO-d6): δ 3.87 (s, 3H), 6.61 (s, 1H), 7.29-7.46 (m, 4H), 10.62 (s, 1H); MS [M+H]+: 336.17.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-188f8b8f93154021a882f39cc43e8ec6
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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