Hydrochloric Acid → HCID 66986879, compound

HRID 2109500Notes

Reaction equation

HRID 2109500 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[CH:17]N(C)C)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C(O)(C)C>[CH2:1]([O:8][C:9]([NH:11][C:12](=[CH:17][N:27]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11487DiphenylamineHCID 66987236HCID 66987236, compound

Product 1

HCID 66986879HCID 66986879, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

36 g (129 mmol) of methyl 2-benzyloxycarbonylamino-3-dimethylaminoacrylate and 24.12 g (142 mmol) of diphenylamine were dissolved in 630 ml of isopropanol at 40° C. Subsequently, the solution was admixed with 17.4 ml of concentrated hydrochloric acid within 5 min and stirred at 40° C. for a further 30 min. The reaction solution was concentrated to 300 ml and admixed slowly with 300 ml of water. The crystallized product was filtered off with suction and dried at 40° C. under reduced pressure. Yield: 30.5 g (59% of theory) 1H NMR: 3.62 (s, 3H), 4.68 (s, 2H), 6.95-7.10 (m, 6H), 7.20-7.50 (m, 9H), 7.61 (s,1 H)

Workup

  1. concentrationThe reaction solution was concentrated to 300 ml
  2. filtrationThe crystallized product was filtered off with suction
  3. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-578e045123cc4cddaf9e4a01e501915c
Source dataset
uspto-grants-2009_04
Patent number
US07514578B2

Reaction notes

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