3-Chloro-1,2-propanediol → HCID 13240419, compound

HRID 2352628Notes

Reaction equation

HRID 2352628 reaction equation
[H-].[Na+].[SH:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[H][H].Cl[CH2:16][CH:17]([OH:20])[CH2:18][OH:19]>CN(C=O)C.[I-].[Na+]>[S:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=[C:4]1[S:3][CH2:16][CH:17]([OH:20])[CH2:18][OH:19]

Participants

7

Reactant 4

HCID 72903-Chloro-1,2-propanediolHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 13240419HCID 13240419, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1.80 g (60 mmol) of an 80% strength NaH/oil dispersion were added (with cooling) to a solution of 10.04 g (60 mmol) of 2-mercaptobenzothiazole in 100 ml of absolute DMF at about 40° C., and the mixture was stirred for 15 minutes at 40° C., after which the evolution of hydrogen was complete. 6.63 g (5.02 ml, 60 mmol) of 1-chloro-2,3-dihydroxypropane and 0.30 g (2 mmol) of powdered sodium iodide were added, the mixture was stirred for 3 hours at 87° C., and the DMF was subsequently substantially removed by distillation in vacuo in a rotary evaporator. The oily residue was taken up in 300 ml of CH2Cl2, and the solution was successively shaken twice with 80 ml of 0.2N NaOH in each case and twice with water, dried, filtered and evaporated in vacuo. The residue remaining, 12.5 g of a viscous oil, was chromatographed on a silica gel S/CH2Cl2 column (diameter 2.0 cm, height 38 cm) by elution with CH2Cl2 and CH2Cl2 /ethanol 100:5-100:3 (v/v) mixtures. The fractions which were unary according to TLC were combined and evaporated vigorously in an oil-pump vacuum. 9.0 g (62.2% of theory) of 1-(benzothiazol-2-ylthio)-2,3-dihydroxypropane, a compound of the formula VIII (Z=S, L, m and p=0), were obtained as a highly viscous oil,

Workup

  1. stirringthe mixture was stirred for 3 hours at 87° C.
  2. customthe DMF was subsequently substantially removed by distillation in vacuo in a rotary evaporator
  3. stirringthe solution was successively shaken twice with 80 ml of 0.2N NaOH in each case and twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. custom12.5 g of a viscous oil, was chromatographed on a silica gel S/CH2Cl2 column (diameter 2.0 cm, height 38 cm) by elution with CH2Cl2 and CH2Cl2 /ethanol 100:5-100:3 (v/v)
  8. customevaporated vigorously in an oil-pump vacuum

Sources & evidence

ORD record
ord-14d48334bcc84e7ab81301af82848620
Source dataset
uspto-grants-1989_10
Patent number
US04877878

Reaction notes

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