Water → HCID 15616319, compound

HRID 2379147Notes

Reaction equation

HRID 2379147 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[C:7]=1[CH3:8].CN(C=O)C.S(Cl)([Cl:22])=O.O>ClCCl>[Cl:22][CH2:2][C:3]1[N:4]=[CH:5][N:6]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 15616318HCID 15616318, compound

Product 1

HCID 15616319HCID 15616319, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4-(hydroxymethyl)-N,N,5-trimethyl-1H-imidazole-1-sulphonamide (2.86 g) in dry dichloromethane (200 ml) containing DMF (0.5 ml) was treated dropwise with a solution of thionyl chloride (1.178 g) in dichloromethane (10 ml). The reaction mixture was cooled in ice during the addition and blanketed with nitrogen. When addition was complete (ca. 5 min), stirring was continued at 0° for a further 30 min. Water (200 ml) was then added and the organic phase was separated, washed with 8% sodium bicarbonate (100 ml), dried and concentrated to give the title compound (2.3 g) as a solid, m.p. 115°-118°.

Workup

  1. temperatureThe reaction mixture was cooled in ice during the addition
  2. additionWhen addition
  3. custom(ca. 5 min)
  4. customthe organic phase was separated
  5. washwashed with 8% sodium bicarbonate (100 ml)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed86c2336eeb4312ba2601fe41c45b5f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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