1,3-Dichloro-2-isothiocyanatobenzene → HCID 178496988, compound

HRID 1898341Notes

Reaction equation

HRID 1898341 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]([Cl: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]([Cl: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 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 67504371Methyl 4,5-diamino-2-hydroxybenzoate

Product 1

HCID 178496988HCID 178496988, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4,5-diamino-2-hydroxybenzoate (0.500 g, 2.74 mmol) in acetonitrile (15.0 mL) was added 1,3-dichloro-2-isothiocyanatobenzene (Intermediate-5, 0.550 g, 2.72 mmol). The reaction mass was stirred at RT for 24 h and N,N-di-isopropyl carbodimide (1.0 mL) was added to it. The reaction mass stirred at RT for 4-6 h. The reaction mass was cooled and filtered to afford 0.500 g of the desired product. 1HNMR (DMSO-d6): δ 3.86 (s, 3H), 6.56 (s, 1H), 7.22 (t, J=7.8 Hz, 1H), 7.38 (s, 1H), 7.52 (d, J=7.8 Hz, 2H), 10.49-10.64 (s, 3H); MS [M+H]+: 352.08.

Workup

  1. stirringThe reaction mass stirred at RT for 4-6 h
  2. temperatureThe reaction mass was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-496fd3abfc944aa1ba959930318e0580
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…