Chloroacetyl chloride → HCID 178489487, compound

HRID 1695598Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[O:8][CH2:9][C:10]2[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:11]=2[N:12]=1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>>[Cl:22][CH2:23][C:24]([NH:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:7]([NH:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=3[O:2][CH3:1])[O:8][CH2:9][C:10]=2[CH:16]=1)=[O:25]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 178489485HCID 178489485, compound

Product 1

HCID 178489487HCID 178489487, compoundYield 52.6%

Procedure

Prepared from N2-(2-methoxy-benzyl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 4) (1.26 g, 4.45 mmol) and chloroacetyl chloride (0.39 ml, 4.89 mmol) according to the procedure described for Example 17. Obtained the title compound as a white solid (842 mg, 42%, HPLC 0.889 min 81%), MS (ISP) m/e=360.3 [(M+H)+] and 362.1 [(M+2+H)+].

Sources & evidence

ORD record: ord-ad4f4ac0920d4596b4b08cb9e9e0b2b1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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