Formaldehyde → HCID 23678959, compound

HRID 446627Notes

Reaction equation

HRID 446627 reaction equation
[CH2:1]=O.[S:3](=[O:6])([OH:5])[O-:4].[Na+:7].[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9]>O>[C:8]([NH:12][CH2:1][S:3]([O-:5])(=[O:4])=[O:6])([CH3:11])([CH3:10])[CH3:9].[Na+:7]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6385Tert-ButylamineHCID 23665763Sodium Bisulfite

Product 1

HCID 23678959HCID 23678959, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
72.5 °C

Procedure

37% Formaldehyde solution (18 g, 0.22 mol) was added to a suspension of sodium bisulfite (22 g, 0.2 mol) in water (25 mL). To this mixture was added tert-butylamine (28 mL, 19.4 g, 0.26 mol) at such a rate that the temperature of the reaction mixture was not exceeding 30° C. When the addition was complete, a distillation apparatus was set and the mixture was stirred at 70-75° C. for 10 minutes (excess of tert-butylamine was distilled off) and cooled to 10-15° C. The formed precipitate was filtered, washed with methanol and dried at 20-25° C. to give sodium tert-butylaminomethylsulfonate (30 g, 80%), as white plates, decomposition without melting above 180-190° C. (smell of amine),

Workup

  1. customwas not exceeding 30° C
  2. additionWhen the addition
  3. distillation(excess of tert-butylamine was distilled off)
  4. temperaturecooled to 10-15° C
  5. filtrationThe formed precipitate was filtered
  6. washwashed with methanol
  7. customdried at 20-25° C.

Sources & evidence

ORD record
ord-a9ade639590c4a6a842b241a6cff4315
Source dataset
uspto-grants-2013_07
Patent number
US08480795B2

Reaction notes

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