Dichloromethane → HCID 23434730, compound

HRID 2122047Notes

Reaction equation

HRID 2122047 reaction equation
CN[CH2:3][CH:4]1[CH2:17][S:16][CH2:15][CH2:14][CH2:13][S:12][CH2:11][CH2:10][S:9][CH2:8][CH2:7][CH2:6][S:5]1.[H][H].OCC1[CH2:35][S:34]CCCSCCSCCCS1.O=S(Cl)Cl.[CH2:40](Cl)[Cl:41]>CO>[Cl:41][CH2:40][CH:10]1[CH2:11][S:12][CH2:13][CH2:14][CH2:15][S:16][CH2:17][CH2:35][S:34][CH2:3][CH2:4][S:5][CH2:6][CH2:7][CH2:8][S:9]1

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 23434726HCID 23434726, compoundHCID 23434729HCID 23434729, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23434730HCID 23434730, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The synthesis of 2-(N-methyl)aminomethyl-1,4,8,11-tetrathiacyclotetradecane 5 (as shown in step B of FIG. 1) is performed by the following method. (In FIG. 1, R1 can be methyl (Me) and R2 can be hydrogen (H).) A solution of the previously synthesized crown 2-hydroxymethyl-1,4,8,11-tetrathiacyclotetradecane (0.8 g, 2.7 mmol) in CH2Cl2 (10 mL) is added dropwise to a solution of SOCl2 (0.64 g, 5.4 mmol) in CH2Cl2 (10 mL). After stirring for six hours, the reaction is treated with methanol (1 mL) to quench the excess SOCl2. The solvent is removed by rotary evaporation to yield 2-chloromethyl-1,4,8,11,14-pentathiacycloheptadecane as a yellow oil. The oil is then dissolved in CH3CN (15 mL) and added dropwise to CH3CN (50 mL) that has been saturated with CH3NH2 at 0° C. and charged with Na2CO3 (0.42 g, 4 mmol). The reaction is stirred for 12 hours and then filtered. The solvent is removed by rotary evaporation to yield a yellow oil. The product is purified by column chromatography on silica gel (eluent: 5% methanol in CHCl3) and is isolated as a light yellow oil (0.54 g, 65%).

Workup

  1. customto quench the excess SOCl2
  2. customThe solvent is removed by rotary evaporation

Sources & evidence

ORD record
ord-e2d8f42b742746dab807538626976a5d
Source dataset
uspto-grants-2004_02
Patent number
US06696576B2

Reaction notes

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