Chloroacetyl chloride → HCID 13689042, compound

HRID 364186Notes

Reaction equation

HRID 364186 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[N:6]=[C:5]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:3]=1[C:4]=23.CCN(CC)CC.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)(Cl)Cl>[Cl:32][CH2:33][C:34]([NH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[N:6]=[C:5]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:3]=1[C:4]=23)=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 13689033HCID 13689033, compound

Product 1

HCID 13689042HCID 13689042, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture of 10.2 g (0.030 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine and 8.3 ml (0.060 mol) of Et3N in 90 ml of CHCl3 was treated dropwise with a solution of 3.6 ml (0.045 mol) of chloroacetyl chloride in 20 ml of CHCl3 over ten minutes. The reaction mixture was stirred at room temperature for three hours, treated with an additional 1.2 ml (0.015 mol) of chloroacetyl chloride in 50 ml of CHCl3, and concentrated to dryness in vacuo. The residue was triturated three times with cold MeOH to give 8.3 g of product, mp 204°-205° C. dec.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe residue was triturated three times with cold MeOH

Sources & evidence

ORD record
ord-11c0c1c911a54ff58349ecdfe45d2e31
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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