Dichloromethane → HCID 23468304, compound

HRID 443648Notes

Reaction equation

HRID 443648 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([N:5]([CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)=[O:4].[N:32]#[C:33]Br.C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[F:1][C:2]([F:30])([F:31])[C:3]([N:5]([CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:33]#[N:32])=[CH:22][CH:21]=1)[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 6451240Aluminum(III) ChlorideHCID 23468288HCID 23468288, compound

Product 1

HCID 23468304HCID 23468304, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.4 g. of ethyl 4-[N-trifluoroacetyl-2-(1-naphthyloxy)ethylamino]benzoate and 1.5 g. of cyanogen bromide in 200 ml. of methylene chloride at -5° C. is added 5.7 g. of anhydrous aluminum chloride. The solution is allowed to stand at room temperature for 5 hours and then poured into 200 ml. of ice and water. After addition of 20 ml. of concentrated hydrochloric acid, the organic layer is seperated, washed with water, dried and evaporated to dryness. Recrystallization from 75% aqueous acetonitrile gives material, m.p. 150°-151° C.

Workup

  1. additionpoured into 200 ml
  2. additionAfter addition of 20 ml
  3. customof concentrated hydrochloric acid, the organic layer is seperated
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness
  7. customRecrystallization from 75% aqueous acetonitrile
  8. customgives material, m.p. 150°-151° C.

Sources & evidence

ORD record
ord-ff530e83b9d743449546c8e458f6432d
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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