Benzyl mercaptan → HCID 16075058, compound

HRID 1609410Notes

Reaction equation

HRID 1609410 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][SH:8])=[CH:3][CH:2]=1.ClN1C(=O)C[CH2:12][C:11]1=[O:16].[SH:17]C(O)C.C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl>[C:4]1([CH2:7][S:8][S:17][CH2:12][CH2:11][OH:16])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 4713212Mercapto-ethanol

Product 1

HCID 16075058HCID 16075058, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of benzylthiol (1.17 ml) in dry toluene (2 ml) was added dropwise over 5 min to a suspension of N-chlorosuccinimide (1.34 g) in toluene (5 ml). The mixture was stirred for 5 min the a mixture of mercaptoethanol (700 μl) and triethylamine (1.34 ml) in toluene (3 ml) was added dropwise over 5 min. The mixture was stirred for a further 10 min the diluted to 30 ml with dichloromethane, washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel eluted with dichloromethane to afford the title compound (522 mg, 25%).

Workup

  1. additionwas added dropwise over 5 min
  2. stirringThe mixture was stirred for a further 10 min the
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with dichloromethane

Sources & evidence

ORD record
ord-61f65302a1cb41eea98642e4432923f1
Source dataset
uspto-grants-1995_03
Patent number
US05401378

Reaction notes

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