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1,3-Bis((2-chloroethyl)sulfonyl)propan-2-ol → HCID 57157305, compound

HRID 434394
Notes
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Reaction equation

HRID 434394 reaction equation
Cl[CH2:2][CH2:3][S:4]([CH2:7][CH:8]([OH:16])[CH2:9][S:10]([CH2:13][CH2:14][Cl:15])(=[O:12])=[O:11])(=[O:6])=[O:5].[CH:17]([S:25]([O-:27])=[O:26])=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>O.CO>[Cl:15][CH2:14][CH2:13][S:10]([CH2:9][CH:8]([OH:16])[CH2:7][S:4]([CH2:3][CH2:2][S:25]([CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:27])=[O:26])(=[O:6])=[O:5])(=[O:12])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 112207101,3-Bis((2-chloroethyl)sulfonyl)propan-2-olHCID 74085937HCID 74085937, compound

Product 1

HCID 57157305HCID 57157305, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
46 °C

Procedure

In a 3 liter reaction vessel were placed 1 liter of distilled water, 1 liter of methanol and 157 g of 1,3-di(2-chloroethylsulfonyl)-2-hydroxypropane. The vessel was heated to 46° C. for the purpose of dissolution. Thereto, a solution of 52 g sodium styrenesulfinate dissolved in a mixture of 100 ml of distilled water and 100 ml of methanol was added dropwise over a period of about 1 hour, and the heating and the stirring were further continued for 5 hours. A crystal deposited was filtered off, washed with methanol, and dried in vacuo. Thus, 55 g of M-6 was obtained. The yield was 49%.

Workup

  1. customIn a 3 liter reaction vessel
  2. additionwas added dropwise over a period of about 1 hour
  3. filtrationA crystal deposited was filtered off
  4. washwashed with methanol
  5. customdried in vacuo
  6. customThus, 55 g of M-6 was obtained

Sources & evidence

ORD record
ord-605952e14ee140f692aaadbc33fe4bc4
Source dataset
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04396708

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes