Hydrochloric Acid → HCID 178493226, compound

HRID 241537Notes

Reaction equation

HRID 241537 reaction equation
[N+]([O-])(O)=O.[NH2:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([O:19][CH3:20])[CH:10]=1)=[NH:7].[ClH:21]>O>[ClH:21].[NH2:7][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:19][CH3:20])[CH:10]=1)=[NH:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178498157HCID 178498157, compound

Product 1

HCID 178493226HCID 178493226, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77.5 °C

Procedure

Into a reactor was added 5 (29.8 kg, 104 mol) and water (475 L). The mixture was heated to 75 to 80° C. and concentrated HCl (107 kg, 1051 mol) was added over a minimum of 30 min while maintaining the temperature between 75 and 80° C. The reaction mixture was stirred for 3 h at 75 to 80° C. The reaction mixture was sampled and the % conversion was determined by HPLC analysis. The mixture was heated at 75 to 80° C. until the % conversion reached >97.3% or until at total reaction time of 7 h. The reaction was cooled to 20 to 25° C. over a minimum of 3 h and stirred for an additional 2 h at 20 to 25° C. The reaction was filtered and washed with 16% w/w HCl (2×35 kg), water (82 L) and heptane (2×120 L). The resulting wet cake was dried under vacuum at 35 to 50° C. to provide 23.9 kg (93% yield) of 6. 1H NMR (300 MHz, DMSO-d6) δ 10.25 (s, 1H), 7.72 (s, 4H), 7.69 (d, J=8.8 Hz, 1H), 6.93 (d, J=2.3 Hz, 1H), 6.81 (dd, J=2.3, 8.8 Hz, 1H), 3.80 (s, 3H); MS (ESI) m/z 210.4 (M+, 100%).

Workup

  1. temperaturewhile maintaining the temperature between 75 and 80° C
  2. aliquotThe reaction mixture was sampled
  3. temperatureThe mixture was heated at 75 to 80° C. until the % conversion
  4. customuntil at total reaction time of 7 h
  5. temperatureThe reaction was cooled to 20 to 25° C. over a minimum of 3 h
  6. stirringstirred for an additional 2 h at 20 to 25° C
  7. filtrationThe reaction was filtered
  8. washwashed with 16% w/w HCl (2×35 kg), water (82 L) and heptane (2×120 L)
  9. customThe resulting wet cake was dried under vacuum at 35 to 50° C.

Sources & evidence

ORD record
ord-21c0fed53dd645c2a33e4bc67853f2c5
Source dataset
uspto-grants-2014_02
Patent number
US08653064B2

Reaction notes

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