Ammonia → 5-AMINO-3-METHYLISOTHIAZOLE-4-CARBOXAMIDE

HRID 1782170Notes

Reaction equation

HRID 1782170 reaction equation
S(=O)(=O)(O)[OH:2].[NH2:6][C:7]1[S:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]#[N:14].N>>[NH2:6][C:7]1[S:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]([NH2:14])=[O:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 14977025-amino-3-methylisothiazole-4-carbonitrile

Product 1

HCID 122550895-AMINO-3-METHYLISOTHIAZOLE-4-CARBOXAMIDEYield 80%

Conditions

Temperature
70 °C

Procedure

To a chilled solution of sulfuric acid (7.2 volumes, 12.9 equivs) was charged 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (1.0 equiv). The temperature was maintained below 55° C. The reaction mixture was heated to 70° C. and held for 1 hour until TLC showed disappearance of starting material. The mixture was cooled to 60-65° C. before the ammonia (21 volumes) was charged to pH 10. The mixture was cooled to 20° C., aged overnight and filtered. The resulting solid was washed with dilute ammonia (3.6 volumes) and dried at 40° C. to give a pale brown solid (typical yield 80%).1H NMR (300 MHz, DMSO-d6) δ 2.46(s, 3H), 6.28 (s, 1H).

Workup

  1. temperatureThe temperature was maintained below 55° C
  2. additionwas charged to pH 10
  3. temperatureThe mixture was cooled to 20° C., aged overnight
  4. filtrationfiltered
  5. washThe resulting solid was washed with dilute ammonia (3.6 volumes)
  6. customdried at 40° C.
  7. customto give a pale brown solid (typical yield 80%)

Sources & evidence

ORD record
ord-a0887a0e8931430f991311bcea63e31a
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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