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

HRID 2280220Notes

Reaction equation

HRID 2280220 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-19aef9039ccf476fb80c76ef475dba84
Source dataset
uspto-grants-2015_09
Patent number
US09138462B2

Reaction notes

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