Ammonia → HCID 55281885, compound

HRID 1782127Notes

Reaction equation

HRID 1782127 reaction equation
[C:1](/[C:3](=[C:7](\OCC)/[CH3:8])/[C:4](=[S:6])[NH2:5])#[N:2].[NH3:12]>CO>[NH2:12]/[C:7](/[CH3:8])=[C:3](\[C:1]#[N:2])/[C:4](=[S:6])[NH2:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2745773116595-42-7

Product 1

HCID 55281885HCID 55281885, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2E)-2-Cyano-3-ethoxybut-2-enethioamide (method 2) (19.2 g, 0.136 mol) was dissolved in a saturated solution of ammonia in methanol (500 mL) and stirred at r.t. overnight. The reaction mixture was concentrated and the residue was dissolved in hot water (600 mL) and the undissoved solid was filtered and dried to recover 6 g of the starting thiocrotonamide. The aqueous solution on standing overnight provided the pure (2E)-3-amino-2-cyanobut-2-enethioamide (6.85 g, 63%) as off-white crystals. 1H NMR (300 MHz, DMSO-d6) δ 2.22 (s, 3H), 7.73 (bs, 1H), 8.53 (bs, 1H), 9.01 (bs, 1H), 11.60 (bs, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in hot water (600 mL)
  3. filtrationthe undissoved solid was filtered
  4. customdried
  5. customto recover 6 g of the starting thiocrotonamide
  6. waitThe aqueous solution on standing overnight

Sources & evidence

ORD record
ord-959a3d40ae2148beae62f7d18c8db73d
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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