O,O-Diethyl dithiophosphate → 2,6-Dihydroxybenzenecarbothioamide

HRID 53574

Reaction equation

HRID 53574 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[S:10])[NH2:9].[OH:11]C1C=CC=C(O)C=1C#N.P(S)(OCC)(OCC)=S>O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:11])[C:3]=1[C:8](=[S:10])[NH2:9]

Participants

5

Reactant 3

HCID 9274O,O-Diethyl dithiophosphateHCID 937912,6-DihydroxybenzonitrileHCID 27593422-Hydroxybenzenecarbothioamide

Product 1

HCID 1357374452,6-DihydroxybenzenecarbothioamideYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure used for the preparation of 3a was repeated with 2,6-dihydroxybenzonitrile (8.75 g, 64.8 mmol), (EtO)2P(S)SH (32.6 mL, 194 mmol) and water (26 mL) at 60° C. for 36 hr to give 3b (4.76 g, 43%) as a light yellow solid after chromatographic purification on silica gel (gradient EtOAc/CH2Cl2 :0-5%) and crystallization from EtOAc/hexane. mp 180° C. (dec); IR (KBr) 3411, 3295, 3177, 2380, 1612, 1577, 1464, 1267, 1010 cm-1 ; 1H NMR (DMSO-d6) δ6.31 (2H, d, J=8.1 Hz, Ar), 7.00 (1H, t, J=8.1Hz, Ar), 9.60 (1H, br s, NH), 9.96 (1H, br s, NH), 10.93 (2H, s, OH); FABMS m/z 169 (M+), 170 (M+ +1); Anal. Calcd for C7H7NO2S: C, 49.69; H, 4,17; N, 8.28. Found: C, 49.89; H, 4.23; N, 8.36.

Sources & evidence

ORD record
ord-01f2f8a8a53d4d1d8fa1d6c058f5497a
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Linked notes

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