Hydrochloric Acid → HCID 86587436, compound

HRID 1357843Notes

Reaction equation

HRID 1357843 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([N:15]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH:16]=[O:17])[CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.Cl.NC1C=CC=CC=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([Cl:47])[CH:46]=1)[C:41](Cl)=[O:42]>ClCCl.CCOCC.CC(N(C)C)=O.C(N(CC)CC)C>[Cl:37][C:38]1[CH:39]=[C:40]([C:41]([NH:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[CH:16]=[O:17])[CH:12]=[CH:13][CH:14]=2)=[O:42])[CH:44]=[C:45]([Cl:47])[CH:46]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 761913,5-Dichlorobenzoyl chlorideHCID 86587437HCID 86587437, compound

Product 1

HCID 86587436HCID 86587436, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 31374DimethylacetamideSolvent

Procedure

{3-[(tert-Butoxy)carbonylamino]phenyl}-N-(naphthylmethyl) formamide (270 mg, 0.72 mmol) was dissolved in 25 ml of dichloromethane and treated with 7 ml of 2N HCl in ether. After stirring overnight, the precipitate was collected by filtration and dried under vacuum. The aniline (190 mg, 0.61 mmol) was dissolved in dimethylacetamide (10 ml), and 3,5-dichlorobenzoyl chloride (130 mg, 0.61 mmol) and triethylamine (0.5 mL) were added and the resulting mixture was stirred overnight. The product was worked up as described above and recrystallized from ethyl acetate to provide compound 16 as a white crystalline solid, Mp=205-208° C., and 1H NMR (DMSO, 400 MHz) peaks of: δ 4.97 (d, 2H, J=5.76); 7.45-8.26 (m, 14H); 9.10 (t, 1H, J=5.76); 10.57 (s, 1H). The theoretical atomic composition for C25H18N2O2Cl2 [C, 66.83; H, 4.04; N, 6.23; Cl, 15.78] compares favorably with that found experimentally [C, 66.73; H, 4.15; N, 6.16; Cl, 15.81].

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried under vacuum
  3. stirringthe resulting mixture was stirred overnight
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-85dbfb8750094016afd37b1cb0269b30
Source dataset
uspto-grants-2003_07
Patent number
US06593362B2

Reaction notes

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