Water → HCID 21512268, compound

HRID 1576360Notes

Reaction equation

HRID 1576360 reaction equation
BrBr.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[S-:17][C:18]#[N:19].[Na+].O>C(O)(=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([S:17][C:18]#[N:19])[C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516871Sodium thiocyanateHCID 21512269HCID 21512269, compound

Product 1

HCID 21512268HCID 21512268, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of 6 ml (0.11 mole) of bromine in 20 ml of acetic acid was added dropwise over 20 min to a stirred mixture of 25 g (0.10 mole) of N-(2,5-dichloropheyl)-β-alanine, 20.5 g (0.25 mole) of sodium thiocyanate and 100 ml of acetic acid at 15°-20°. An additional 80 ml of acetic acid was added to facilitate stirring which was continued for 1 hr. The reaction mixture was poured into 600 ml of cold water. The yellow solid was collected by filtration, washed with water and dried in an oven at 100° for 2 hrs to give 30 g (100%) of N-(2,5-dichloro-4-thiocyanatophenyl)-β-alanine. Two recrystallizations from CH3NO2 gave an analytical sample, m.p. 133°-135°.

Workup

  1. filtrationThe yellow solid was collected by filtration
  2. washwashed with water
  3. customdried in an oven at 100° for 2 hrs

Sources & evidence

ORD record
ord-d239f70af1f4442a83fe680f446774ec
Source dataset
uspto-grants-1976_09
Patent number
US03980689

Reaction notes

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