Triphosgene → (S)-4-[2-Hydroxy-3-(N,N-dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1601457Notes

Reaction equation

HRID 1601457 reaction equation
[CH2:1]([N:8]([CH2:16][C@H:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[C:21]=1[NH2:27])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1.Cl>[OH:28][C@@H:17]([CH2:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:18][O:19][C:20]1[C:21]2[NH:27][C:30](=[O:32])[NH:26][C:22]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 54261304(2S)-1-(2,3-Diaminophenoxy)-3-(dibenzylamino)propan-2-ol

Product 1

HCID 54425116(S)-4-[2-Hydroxy-3-(N,N-dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

(S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2,3-diaminobenzene (4.4 g, 11.6 mmol) was suspended in a mixture of toluene (60 mL) and 2N HCl (100 mL) at ambient temperature with vigorous stirring. An excess of triphosgene (17.3 g, 58.3 mmol) was added, and the stirring continued for 14 hours. The biphasic mixture was cautiously quenched and neutralized with sodium bicarbonate, causing an off-white precipitate to form at the interface. The precipitate was filtered and dried in vacuo to yield 4.35 g (93%) of a pale solid that was used without further purification. TLC, NMR and MS all indicated high purity of the intermediate.

Workup

  1. customThe biphasic mixture was cautiously quenched
  2. customto form at the interface
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7d8314b2b95d4e388d6a184da1d76442
Source dataset
uspto-grants-1999_11
Patent number
US05977154

Reaction notes

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