Sulfuric Acid → 2,6-Bis(hydroxymethyl)-4-(phenylsulfonyl)morpholine

HRID 500485Notes

Reaction equation

HRID 500485 reaction equation
[O:1]1CCCC1.[O:6]1[CH2:8][CH:7]1[CH2:9][N:10]([CH2:20][CH:21]1[CH2:23][O:22]1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].S(=O)(=O)(O)O.[Cl-].[Na+]>C(OCC)(=O)C>[OH:22][CH2:23][CH:21]1[O:1][CH:7]([CH2:8][OH:6])[CH2:9][N:10]([S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH2:20]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 11207928N,N-bis(2-oxiranylmethyl)benzenesulfonamide

Product 1

HCID 185403742,6-Bis(hydroxymethyl)-4-(phenylsulfonyl)morpholine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tetrahydrofuran (40 mL) was added to N,N-bis(2-oxiranylmethyl)benzenesulfonamide (from step (i) (alternative A) above; 10 g, 37.1 mmol), followed by dilute sulfuric acid (10 mL of 1 M), and the mixture stirred for 6 days (reaction is complete within 1 day). Solid sodium chloride (3 g) and ethyl acetate (40 mL) were added, and the mixture stirred for 1 hour. The organic phase was separated and washed with aqueous ammonium chloride (10 mL of 10%). The organic phase was concentrated under reduced pressure before toluene was added (50 mL). The mixture was concentrated again to leave the title compound as a crude oil (10.65 g). This material was employed directly in subsequent reactions without any further purification.

Workup

  1. custom(reaction is complete within 1 day)
  2. stirringthe mixture stirred for 1 hour
  3. customThe organic phase was separated
  4. washwashed with aqueous ammonium chloride (10 mL of 10%)
  5. concentrationThe organic phase was concentrated under reduced pressure before toluene
  6. additionwas added (50 mL)
  7. concentrationThe mixture was concentrated again

Sources & evidence

ORD record
ord-b9f6ba6be9ef422aae17f4b196513d00
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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