2-Bromoethyl isocyanate → HCID 86596235, compound

HRID 658087Notes

Reaction equation

HRID 658087 reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])=[O:5].[Br:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21]>CN(C=O)C>[Br:16][CH2:17][CH2:18][NH:19][C:20]([S:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])=[O:5])=[O:21]

Participants

4

Reactant 2

HCID 42559572-Bromoethyl isocyanateHCID 69048570HCID 69048570, compound

Product 1

HCID 86596235HCID 86596235, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-mercaptobenzoyl)-β-alaninamide (0.90 g, 4.0 mmol) in DMF (20 ml) was added 2-bromoethyl isocyanate (0.91 g, 6.0 mmol). The reaction mixture was stirred for 6 h. The solvent was evaporated to dryness, and the residue was treated with ethyl ether (20 ml) with vigorous stirring. The precipitate obtained was filtered, washed with water and dried over CaCl2. Yield: 87%. 1H NMR (DMSO-d6): 2.36 (t, 2H, CH2), 3.42 (q, 2H, CH2), 3.54 (s, 4H, 2CH2), 6.88 (brs, 1H, NH2), 7.36-7.66 (m, 5H, Ar—H, NH2), 8.26 (t, 1H, NH), 8.66 (brs, 1H, NH).

Workup

  1. customThe solvent was evaporated to dryness
  2. additionthe residue was treated with ethyl ether (20 ml) with vigorous stirring
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. dry with materialdried over CaCl2

Sources & evidence

ORD record
ord-360c2035af9a41969284049f7d8d52b2
Source dataset
uspto-grants-2011_12
Patent number
US08076372B2

Reaction notes

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