Guanidine Hydrochloride → 10065-79-9

HRID 1470233Notes

Reaction equation

HRID 1470233 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.Cl.[NH2:7][C:8]([NH2:10])=[NH:9].[OH-:11].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O>[CH2:17]([O:16][C:14]([NH:9][C:8]([NH:10][C:3]([O:4][CH2:5][C:1]1[CH:2]=[CH:3][CH:2]=[CH:1][CH:5]=1)=[O:11])=[NH:7])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 13783255110065-79-9

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A 100 L glass lined reactor equipped with a mechanical agitator, cooling jacket, condenser, and addition lines was charged with THF (15.53 kg) and guanidine HCl (3.10 kg, 32.02 mol). To the resultant slurry was added purified water (5.00 kg) and 50% sodium hydroxide solution (8.61 kg, 100.75 mol). The resultant slurry was cooled to 4-6° C. and benzyl chloroformate (13.02 kg, 72.51 mol) was slowly added over a 3.5-hour period, while keeping the temperature below 10° C. The resultant slurry was stirred for 2 hours at a temperature between 5-10° C. The slurry was then filtered and the solids washed with THF (5.58 kg).

Workup

  1. customequipped with a mechanical agitator
  2. temperaturecooling
  3. additionjacket, condenser, and addition lines
  4. additionTo the resultant slurry was added
  5. customthe temperature below 10° C
  6. filtrationThe slurry was then filtered
  7. washthe solids washed with THF (5.58 kg)

Sources & evidence

ORD record
ord-7f7a19a474874dc6af10fb8d83baae3e
Source dataset
uspto-grants-2015_04
Patent number
US09006432B2

Reaction notes

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