Thionyl Chloride → HCID 87145630, compound

HRID 1644133Notes

Reaction equation

HRID 1644133 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([S:6][CH2:7][C:8]1([CH:16]=[CH:15][CH:14]=[CH:13][CH2:12]1)[C:9](O)=[O:10])=[S:5])[CH3:2].S(Cl)([Cl:21])=O>ClCCl>[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([S:6][CH2:7][C:8]1([CH:16]=[CH:15][CH:14]=[CH:13][CH2:12]1)[C:9]([Cl:21])=[O:10])=[S:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86618659HCID 86618659, compound

Product 1

HCID 87145630HCID 87145630, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-((Diethylcarbamothioylthio)methyl)benzoic acid (0.1 g) was refluxed in a solution of thionyl chloride (1 mL, in excess) and dichloromethane (10 mL) for 2 h. The reaction was then evaporated to dryness and the product obtained as a pale yellow liquid (yield 100%). The product was diluted with dichloromethane to a volume of 1.00 mL (standard solution of 0.353 M) for subsequent reaction with OH terminated Star-PEG MW 116,000 (see below). Conversion of the carboxylic acid to the acid chloride was further verified by the observation that the starting material was a white solid, which was partially insoluble in dichloromethane, whilst the product was a pale, yellow liquid which was completely soluble in dichloromethane. 1H NMR (CD2Cl2, 400 MHz) δ 1.27-1.29 (br.m, 6H, 2×CH3), 3.76 (br.q, J=7.0 Hz, 2H, CH2N), 4.04 (br.q, J=7.0 Hz, 2H, CH2N), 4.66 (s, 2H, CH2S), 7.53 (d, J=8.4 Hz, 2H, aromatic, 8.04 (d, J=8.4 Hz, 2H, aromatic) ppm. 13C(CD2Cl2, 400 MHz) δ 11.8, 12.9, 41.3, 47.5, 50.5, 53.5, 53.7, 54.0, 54.3, 54.5, 130.4, 132.0, 132.5, 146.6, 168.4, 194.3 ppm.

Workup

  1. customThe reaction was then evaporated to dryness

Sources & evidence

ORD record
ord-305e029c1e284eee8d81d1dd8eb887c3
Source dataset
uspto-grants-2012_02
Patent number
US08124188B2

Reaction notes

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