Water → HCID 19769831, compound

HRID 1723282Notes

Reaction equation

HRID 1723282 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[NH:26][CH:25]=[N:24][C:23]=1[CH2:27][CH:28]1[C:40](=[O:41])[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]=2[CH2:30][CH2:29]1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:21][C:22]1[N:26]([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[N:24][C:23]=1[CH2:27][CH:28]1[C:40](=[O:41])[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]=2[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 19769823HCID 19769823, compound

Product 1

HCID 19769831HCID 19769831, compoundYield 137.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triphenylchloromethane (4.2 g) in dry DMF (40 ml) was added dropwise to a solution of 1,2,3,9-tetrahydro-3-[(5-methyl-1H-imidazol-4-yl)methyl]-4H-carbazol-4-one (3.5 g) and triethylamine (1.75 ml) in dry DMF (35 ml) under nitrogen. After stirring for 4 h the mixture was poured into water (300 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (200 ml), dried and evaporated to give an oil (ca. 9 g) which was purified by FCC eluting with System A (200:10:1) to give the title compound (4.57 g) as a foam, t.l.c. (System A 200:10:1) Rf 0.32.

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. washThe combined extracts were washed with water (200 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-34ad5ce4609c416da10d6a16615bfc06
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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