Benzenemethanethiol, alpha,alpha-diphenyl- → HCID 66603941, compound

HRID 1776125Notes

Reaction equation

HRID 1776125 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)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:49]=[CH:48][CH:47]=[C:41]2[C:42]([NH:44][C:45](=[O:46])[C:40]=12)=[O:43]>CS(C)=O>[C:7]([S:8][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:49]=[CH:48][CH:47]=[C:41]2[C:42]([NH:44][C:45](=[O:46])[C:40]=12)=[O:43])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219308536-Bromohexylphthalimide

Product 1

HCID 66603941HCID 66603941, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triphenylmethanethiol (11.90 g, 43.08 mmol) was suspended in DMSO (40 mL). DBU (7.41 mL, 49.55 mmol) and 6-bromohexylphthalimide (13.32 g, 42.94 mmol) were added, and the mixture was allowed to react for approximately 15 min. The reaction mixture was partitioned between ethyl acetate (700 mL) and 0.1 M HCl (200 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL), and the combined organic fractions were washed with NaHCO3 sat. (80 mL) and brine (80 mL), dried over MgSO4, filtered and concentrated. The crude yellow oil was recrystallized from n-heptane/ethyl acetate. The intermediate 6-(S-Trityl-)mercaptohexylphthalimide was obtained as a white solid (13.3 g, 26.4 mmol, 62%).

Workup

  1. customto react for approximately 15 min
  2. customThe reaction mixture was partitioned between ethyl acetate (700 mL) and 0.1 M HCl (200 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organic fractions were washed with NaHCO3 sat. (80 mL) and brine (80 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude yellow oil was recrystallized from n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-15408f87506648d48a6b2195fff31bea
Source dataset
uspto-grants-2016_02
Patent number
US09265723B2

Reaction notes

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