Methylamine → HCID 178485071, compound

HRID 1733493Notes

Reaction equation

HRID 1733493 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([NH:8][C:9]([NH2:11])=[NH:10])[S:5][N:4]=1.Cl.[NH2:13][CH2:14][CH2:15][SH:16].[OH-].[Na+].CO[C:21](OC)=[N:22][C:23]#[N:24].[CH3:27][NH2:28]>C(O)C.O>[C:27]([N:24]=[C:23]([NH:22][CH3:21])[NH:13][CH2:14][CH2:15][S:16][CH2:2][C:3]1[N:7]=[C:6]([NH:8][C:9]([NH2:11])=[NH:10])[S:5][N:4]=1)#[N:28]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 90604Carbonimidic acid, N-cyano-, dimethyl esterHCID 178512678HCID 178512678, compound

Product 1

HCID 178485071HCID 178485071, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Pure 3-chloromethyl-5-guanidino-1,2,4-thiadiazole (150 g.) was stirred in ethanol (600 ml.) at 10° and 2-aminoethanethiol hydrochloride (93 g.) added. 18 N NaOH (92 ml.) diluted with water (300 ml.) was then added over 30 minutes at 10°-15°. After 90 minutes further water (600 ml.) was added and the solution was stirred for a further 30 minutes before dimethyl (N-cyanoimido)carbonate (107 g.) was added. The resulting solution was stirred for 60 minutes and then aqueous methylamine (40% w/w, 660 ml.) was added. The mixture was stirred for 18 hours and the product removed by filtration and washed with ethanol/water (1:1 v/v, 2×250 ml.) (164 g., 67%). Crystallisation from ethanol/water 3:1 v/v gave 3-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]-5-guanidino-1,2,4-thiadiazole.

Workup

  1. additionwas then added over 30 minutes at 10°-15°
  2. additionwas added
  3. stirringThe mixture was stirred for 18 hours
  4. customthe product removed by filtration
  5. washwashed with ethanol/water (1:1 v/v, 2×250 ml.) (164 g., 67%)
  6. customCrystallisation from ethanol/water 3:1 v/v

Sources & evidence

ORD record
ord-11759cc192a64d8bba78c504dc077e49
Source dataset
uspto-grants-1980_12
Patent number
US04242350

Reaction notes

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